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Chemical Structure| 40682-54-0
Chemical Structure| 40682-54-0
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Product Details of [ 40682-54-0 ]

CAS No. :40682-54-0 MDL No. :MFCD00206541
Formula : C11H13NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :PRQUMJAKVLLZHP-UHFFFAOYSA-N
M.W : 191.23 Pubchem ID :357745
Synonyms :

Safety of [ 40682-54-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 40682-54-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 40682-54-0 ]

[ 40682-54-0 ] Synthesis Path-Downstream   1~85

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  • [ 37465-31-9 ]
  • [ 120355-29-5 ]
  • 5
  • [ 40682-54-0 ]
  • [ 147720-85-2 ]
  • [ 147720-93-2 ]
  • 6
  • [ 40682-54-0 ]
  • [ 147720-88-5 ]
  • [ 143154-20-5 ]
  • 7
  • [ 40682-54-0 ]
  • [ 100-39-0 ]
  • [ 78843-66-0 ]
  • 8
  • [ 623-33-6 ]
  • [ 100-52-7 ]
  • [ 40682-54-0 ]
YieldReaction ConditionsOperation in experiment
94% With magnesium sulfate; triethylamine; In dichloromethane; at 20℃; for 8h; General procedure: To a 25 mL flask were added aldehyde 7a-j (3 mmol), ethyl glycinate hydrochloride 8a (0.63 g,4.5 mmol), Et3N (0.62 mL, 4.5 mmol), MgSO4 (0.54 g, 4.5 mmol) and CH2Cl2 (10 mL). Themixture was stirred vigorously at room temperature for 8 h. The mixture was filtered, the filtratewas added 20 mL water and extracted with CH2Cl2 (3 × 10 mL). The combined organic phase waswashed with brine, dried over anhydrous Na2SO4, evaporated in vacuo to remaining about 10 mL.Then, to the residue were added maleimide (2 mmol), AgOAc (0.03 g, 0.2 mmol) and Et3N (28 muL,0.2 mmol), the mixture was stirred vigorously at room temperature for 3 h and filtered; the filtratewas evaporated in vacuo. Toluene (10 mL) and DDQ (1.82 g, 8 mmol) were added into the aboveresulted residue. The mixture was stirred vigorously at room temperature for 12-80 h andquenched with 20 mL saturated sodium bicarbonate solution, extracted with CH2Cl2 (6 × 20 mL).The combined organic phase was washed with brine, dried over anhydrous Na2SO4, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with petroleum/ethyl acetate (5:1 to 1:1) to give the target products 12a-k.
94% To a suspension of the corresponding amino acid ester hydrochloride (1.20 equiv) and MgSO4 (1.25 equiv) in dry CH2Cl2 (25 mL) was added Et3N (1.20 equiv). The mixture was stirred at room temperature for 1 h and then the corresponding aldehyde (1.00 equiv) was added. The reaction was stirred at room temperature overnight. The resulting precipitate was removed by filtration. The filtrate was washed with water (15 mL), the aqueous phase was extracted with CH2Cl2 (3 × 30 mL), and the combined organic phases were washed with brine (3 × 30 mL),dried over MgSO4 and concentrated. The resulting imino esters were obtained of sufficient purity to be used for kinetic measurements and product studies without further purification. Ethyl N-benzylideneglycinate (1c-H) was synthesized according to GP 1 from benzaldehyde(2.0 mL, 20 mmol), ethyl glycinate hydrochloride (3.33 g, 2 mmol), MgSO4 (3.0 g, 25 mmol),and Et3N (3.3 mL, 24 mmol): 1c-H (3.60 g, 94%) was obtained as clear yellow oil. 1H-NMRspectroscopic data were in agreement with the literature.
With sodium sulfate; triethylamine; In tert-butyl methyl ether; at 0 - 20℃; for 48.5h; <strong>[623-33-6]Glycine ethyl ester hydrochloride</strong> (304 g, 2.16 mole) was suspended in tert-butylmethyl ether (1.6 L). Benzaldehyde (231 g, 2.16 mole) and anhydrous sodium sulfate (155 g, 1.09 mole) were added, and the mixture was cooled to 0 C. using an ice-water bath. Triethylamine (455 mL, 3.26 mole) was added dropwise over 30 minutes and the mixture was stirred for 48 hours at room temperature. The reaction was then quenched by addition of ice-cold water (1 L) and the organic layer was separated. The aqueous phase was extracted with tert-butylmethyl ether (0.5 L) and the organic phases were combined and washed with a mixture of saturated aqueous NaHCO3 (1 L) and brine (1 L). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to provide 392.4 g of the N-benzyl imine product as a thick yellow oil that was used directly in the next step. 1H NMR (CDCl3, 300 MHz) delta 1.32 (t, J=7.1 Hz, 3H), 4.24 (q, J=7.1 Hz, 2H), 4.41 (d, J=1.1 Hz, 2H), 7.39-7.47 (m, 3H), 7.78-7.81 (m, 2H), 8.31 (s, 1H).
With sodium sulfate; triethylamine; In tert-butyl methyl ether; at 0 - 20℃; for 48.5h; Method A A. 1 Preparation of N-Benzyl Imine of Glycine Ethyl Ester <strong>[623-33-6]Glycine ethyl ester hydrochloride</strong> (303.8 g, 2. 16 mole) was suspended in tert- butylmethyl ether (1.6 L). Benzaldehyde (231 g, 2.16 mole) and anhydrous sodium sulfate (154.6 g, 1.09 mole) were added and the mixture cooled to 0 C using an ice- water bath. Triethylamine (455 mL, 3.26 mole) was added dropwise over 30 min and the mixture stirred for 48 h at rt. The reaction was then quenched by addition of ice- cold water (1 L) and the organic layer was separated. The aqueous phase was extracted with tert-butylmethyl ether (0.5 L) and the combined organic phases washed with a mixture of saturated aqueous NaHCO3 (1 L) and brine (1 L). The solution was dried over MgS04, concentrated in vacuo to afford 392.4 g of the N benzyl imine product as a thick yellow oil that was used directly in the next step. IH NMR (CDCl3, 300 MHz) 8 1.32 (t, J=7. 1 Hz, 3H), 4.24 (q, J=7. 1 Hz, 2H), 4.41 (d, J l. l Hz, 2H), 7.39-7. 47 (m, 3H), 7.78-7. 81 (m, 2H), 8.31 (s, 1H).
With sodium sulfate; triethylamine; In tert-butyl methyl ether; at 0 - 25℃; for 24h; A mixture of benzaldehyde 2-1 (95.6 mL, 943 mmol), <strong>[623-33-6]glycine ethyl ester hydrochloride</strong> 2-2 (131 g, 943 mmol) and Na2504 (80 g, 565 mmol) in MTBE (900 mL) was cooled to 0 C, and then triethylamine (197 mL, 1414 mmol) was added slowly. After the addition, the mixture was warmed to 25 C and stirred for 24 hours. The mixture was filtered by a diatomite filter. The filtrate was concentrated in vacuo to afford a crude product 2-3, which was used in next step without further purification. 1H NIVIR (600 MHz, CDC13): (5 8.28 (s, 1H), 7.86-7.71 (m, 2H), 7.50-7.32 (m, 3H), 4.47-4.32 (m, 2H), 4.29-4.18 (m, 2H), 1.32-1.22 (m, 3H)ppm.
With triethylamine; In toluene; for 2h; 1.In 1000ml reaction flask into 66g (0.62mol) of benzaldehyde, 95.2g (0.68mol) <strong>[623-33-6]glycine ethyl ester hydrochloride</strong>, 200ml of toluene, stir, dropping 68.8g triethylamine. End of the dropwise addition, the reaction was kept for 2 hours.2.Into 200ml water, stirring Still stratification points to the aqueous layer.3.Concentrated under reduced pressure to give compound 4,.

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  • [ 106-95-6 ]
  • [ 119933-90-3 ]
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  • [ 109918-38-9 ]
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  • [ 114461-07-3 ]
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  • [ 122-59-8 ]
  • [ 77821-69-3 ]
  • 15
  • [ 40682-54-0 ]
  • [ 70591-46-7 ]
  • ((S)-3-Methoxycarbonylmethyl-4,4-dimethyl-5-oxo-cyclohexyl)-[1-phenyl-meth-(E)-ylidene]-amino}-acetic acid ethyl ester [ No CAS ]
  • 16
  • [ 40682-54-0 ]
  • [ 105703-61-5 ]
  • 5-ethoxycarbonyl-4-methoxycarbonyl-2-phenyl-spiro-[3H-indol-3,2'-pyrrolidin]-2(1H)-one [ No CAS ]
  • 17
  • [ 40682-54-0 ]
  • (E)-1-methoxy-4-(2-nitrovinyl)benzene [ No CAS ]
  • ethyl 3-(4-methoxyphenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate [ No CAS ]
  • 18
  • [ 18942-89-7 ]
  • [ 40682-54-0 ]
  • ethyl 4-nitro-5-phenylpyrrolidine-2-carboxylate [ No CAS ]
  • 19
  • [ 40682-54-0 ]
  • [ 101671-01-6 ]
  • (2S,3R,4S,5S)-3-(4-Chloro-phenyl)-4-nitro-5-phenyl-pyrrolidine-2-carboxylic acid ethyl ester [ No CAS ]
  • 20
  • [ 40682-54-0 ]
  • [ 247222-86-2 ]
  • 2-benzylamino-3-(2-ethylsulfanyl-1<i>H</i>-indol-3-yl)-propionic acid ethyl ester [ No CAS ]
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  • [ 40682-54-0 ]
  • (+/-)-(2S,3R,5R,6S)-3,5,6-triphenyl-2-hydrogeno-2-oxo-1,4,2-oxazaphosphinane [ No CAS ]
  • (2SR,3RS,5RS,6SR)-(+/-)-ethyl (1-(3,5,6-triphenyl-2-oxo-1,4,2-oxazaphosphinan-2-yl)benzyl)carbamate [ No CAS ]
  • 22
  • [ 821-06-7 ]
  • [ 40682-54-0 ]
  • rac-(1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
A. 2 Preparation of racemic N-Boc-(lR, 2S)/(lS, 2R)-1-amino-2- vinylcyclopropane carboxylic acid ethyl ester; To a suspension of lithium tert-butoxide (84.06 g, 1.05 mol) in dry toluene (1.2 L), was added dropwise a mixture of the N-benzyl imine of glycine ethyl ester (100.4 g, 0.526 mol) and trans-1, 4-dibromo-2-butene (107.0 g, 0.500 mol) in dry toluene (0.6 L) over 60 min. After completion of the addition, the deep red mixture was quenched by addition of water (1 L) and tert-butylmethyl ether (TBME, 1 L). The aqueous phase was separated and extracted a second time with TBME (1 L). The organic phases were combined, 1 N HCl (1 L) was added and the mixture stirred at room temperature for 2 h. The organic phase was separated and extracted with water (0.8 L). The aqueous phases were then combined, saturated with salt (700 g), TBME (1 L) was added and the mixture cooled to 0 C. The stirred mixture was then basified to pH 14 by the dropwise addition of 10 N NaOH, the organic layer separated, and the aqueous phase extracted with TBME (2 x 500 mL). The combined organic extracts were dried (MgS04) and concentrated to a volume of 1L. To this solution of free amine, was added BOC20 or di-tert-butyldicarbonate (131. 0 g, 0.6 mol) and the mixture stirred 4 days at rt. Additional di-tert-butyldicarbonate (50 g, 0.23 mol) was added to the reaction, the mixture refluxed for 3 h, and was then allowed cool to room temperature overnight. The reaction mixture was dried over MgS04 and concentrated in vacuo to afford 80 g of crude material. This residue was purified by flash chromatography (2.5 Kg of si02, eluted with 1% to 2% MeOH/CH2Ck) to afford 57 g (53%) of racemic N-Boc-(lR, 22/(lS, 2R)-l-amino-2-vinylcyclopropane carboxylic acid ethyl ester as a yellow oil which solidified while sitting in the refrigerator : 1H NMR (CDC13, 300 MHz) 8 1.26 (t, J=7. 1 Hz, 3H), 1.46 (s, 9H), 1.43-1. 49 (m, 1H), 1.76-1. 82 (br m, 1H), 2.14 (q, J=8.6 Hz, 1H), 4.18 (q, J=7. 2 Hz, 2H), 5.12 (dd J=10. 3,1. 7 Hz, 1H), 5.25 (br s, 1H), 5.29 (dd, J=17. 6,1. 7 Hz, 1H), 5.77 (ddd, J=17. 6,10. 3, 8. 9 Hz, 1H) ; MS salt 254. 16 (M-1)
  • 23
  • [ 5162-44-7 ]
  • hexamethyl phosphoramide (HMPA) [ No CAS ]
  • [ 40682-54-0 ]
  • ammonium chloride [ No CAS ]
  • [ 114831-24-2 ]
YieldReaction ConditionsOperation in experiment
76% With n-butyllithium; diisopropylamine; In tetrahydrofuran; Ethyl 2-(N-benzylidene)aminohex-2-ene-oate (6) Diisopropylamine (80.2 ml, 0.57M) is added to anhydrous THF (500 ml) and cooled to -10 C. Then 2.4M n-BuLi (237.5 ml) is added slowly, keeping the temperature at -10 C. After complete addition the orange reaction mixture is cooled at -10 C. and stirred for another 15 minutes before reducing the temperature to -78 C. Hexamethyl phosphoramide (HMPA) (100 ml, 0.57M) is then added, followed by the addition of ethyl N-benzylidene glycinate (100 g, 0.52M) dissolved in anhydrous THF (200 ml). After the addition is complete, the reaction mixture is stirred at -78 C. for an additional 15 minutes before adding 4-bromo-1-butene (5) (70.7 g, 0.52M). The reaction mixture is allowed to warm to room temperature and stirring is continued for another 4 hours. It is then poured into ice cold 5% NH4 Cl solution (1 l) and extracted with CHCl3 (3*600 ml). The combined extracts are backwashed with H2 O (3*200 ml), saturated NaCl solution (3*200 ml), dried over anhydrous MgSO4, filtered and evaporated to yield an orange oil. This oil was kugelrohred and the desired product collected to give 97.1 g (76% yield) of (6). 'H-N.M.R. (CDCl3 /TMS): δ=1.28 (t, 3H, --CH2 CH3); 1.97-2.20 (m, 4H, --CH2 --CH2 --); 3.82-4.18 (apparent m, 1H, >CH--CO2 Et, overlaps ethyl ester quartet); 4.25 (q, 2H, --CH2 CH3); 4.80-5.25 (m, 2H, --CH=CH2); 5.33-6.19 (m, 1H, --CH=CH2); 7.10-7.94 (m, 5H, Ph); 8.28 ppm (s, 1H, --N=CH--).
  • 24
  • [ 114831-19-5 ]
  • [ 40682-54-0 ]
  • [ 114831-20-8 ]
YieldReaction ConditionsOperation in experiment
72% With hydrogenchloride; n-butyllithium; diisopropylamine; In tetrahydrofuran; 2-amino-3-hydroxy-6-(N-benzoyl)aminoheptanedioic acid, diethyl ester (9) Diisopropylamine (2.34 ml, 16.7 mmoles) is added to anhydrous THF (75 ml) and cooled to -10 C. At this point 2.24M n-BuLi (6.8 ml, 15.2 mmoles) is added slowly. After complete addition the reaction mixture is stirred for 10 minutes before being cooled to -78 C. At that temperature <strong>[40682-54-0]ethyl N-benzylideneglycinate</strong> (4) (2.9 g, 15.2 mmoles) is added and stirring is allowed to proceed for 15 minutes before aldehyde (8) (4.0 g, 15.2 mmoles), dissolved in anhydrous THF (25 ml), is added dropwise to the yellow anion. After complete addition the reaction is stirred another 11/2 hours before being poured into cold 5% aqueous NH4 Cl. This mixture is extracted with CHCl3 (3*100 ml). The combined extracts are washed with saturated aqueous NaCl, dried over MgSO4, filtered and evaporated to dryness. The oily residue is taken up in THF (300 ml) and shaken with 5% aqueous HCl (200 ml) in a separatory funnel. This mixture is washed with Et2 O (3*100 ml), basified with solid NaHCO3 and extracted with CHCl3 (3*150 ml). The combined extracts are washed with saturated aqueous NaCl (1*150 ml), dried over MgSO4, filtered and evaporated to dryness in vacuo to yield 4.0 g (72% yield) of the desired compound as a yellow glass. 'H-N.M.R. (CHCl3 /TMS): δ=1.20 (t, 3H, --CH2 CH3); 1.28 (t, 3H, --CH2 CH3); 1.45-2.20 (m, 4H, --CH2 CH2 --); 2.46 (broad s, 2H, --NH2); 3.18-4.00 (m, 2H, >CH--NH2, CHOH); 4.19 (q, 2H, --CH2 CH3); 4.25 (q, 2H, --CH2 CH3); 4.53-5.08 (m, 1H, >CH--NH--); 7.05-7.97 ppm (m, 5H, Ph).
  • 25
  • [ 1165938-88-4 ]
  • [ 40682-54-0 ]
  • ethyl 5-phenyl-3-(thiophen-2-yl)-4-((E)-3-(thiophen-2-yl)acryloyl)-pyrrolidine-2-carboxylate [ No CAS ]
  • 26
  • [ 1046149-74-9 ]
  • [ 40682-54-0 ]
  • ethyl 3-(4-methylthiazol-5-yl)-4-((E)-3-(4-methylthiazol-5-yl)acryloyl)-5-phenylpyrrolidine-2-carboxylate [ No CAS ]
  • 27
  • [ 53712-48-4 ]
  • [ 40682-54-0 ]
  • ethyl 3,5-diphenyl-4-((E)-3-phenylacryloyl)-pyrrolidine-2-carboxylate [ No CAS ]
  • 28
  • [ 222159-48-0 ]
  • [ 40682-54-0 ]
  • ethyl 3-(2-chlorophenyl)-4-((E)-3-(2-chlorophenyl)acryloyl)-5-phenylpyrrolidine-2-carboxylate [ No CAS ]
  • 29
  • [ 1165938-89-5 ]
  • [ 40682-54-0 ]
  • ethyl 3-(4-fluorophenyl)-4-((E)-3-(4-fluorophenyl)acryloyl)-5-phenylpyrrolidine-2-carboxylate [ No CAS ]
  • 30
  • [ 124081-76-1 ]
  • [ 40682-54-0 ]
  • ethyl 5-phenyl-3-(p-tolyl)-4-((E)-3-p-tolylacryloyl)pyrrolidine-2-carboxylate [ No CAS ]
  • 31
  • [ 40682-54-0 ]
  • [ 102-96-5 ]
  • C19H20N2O4 [ No CAS ]
  • 32
  • [ 821-06-7 ]
  • [ 40682-54-0 ]
  • [ 787548-29-2 ]
YieldReaction ConditionsOperation in experiment
85% 1.In 1000ml reaction flask into 400ml of toluene, 72g (1.06mol) of sodium in ethanol, feed the end, down to a temperature of ≦ 0 .2.Control of the reaction liquid temperature ≦ 0 , turn into 112.7g (0.53mol) trans-1,4-dibromo-butene, compound 4, the end of the feeding, the reaction was kept for 2 hours.3.Controlling the temperature of ≦ 30 , dropwise addition of 200ml of water, and then controlling the internal temperature was added dropwise 57g 0 ~ 30 hydrochloric acid. Completion of the dropping, stirring insulation. Still stratification aqueous layer was separated.4.The aqueous layer was put into 300ml of toluene, stirring solution of 70g of liquid caustic soda. Completion of dropping, stirring after incubation standing layered organic layer was separated. The organic layer is 3 / toluene solution of the compound in a yield of 85%.
To a suspension of lithium tert-butoxide (84.1 g, 1.05 mol) in dry toluene (1.2 L), was added dropwise a mixture of the N-benzyl imine of glycine ethyl ester (100 g, 0.526 mol) and trans-1,4-dibromo-2-butene (107 g, 0.500 mol) in dry toluene (0.6 L) over 60 minutes. Upon completion of the addition, the deep red mixture was quenched by addition of water (1 L) and tert-butylmethyl ether (TBME, 1 L). The aqueous phase was separated and extracted a second time with TBME (1 L). The organic phases were combined, 1.0M HCl (1 L) was added and the mixture stirred at room temperature for 2 hours. The organic phase was separated and extracted with water (0.8 L). The aqueous phases were then combined, saturated with salt (700 g), and TBME (1 L) was added and the mixture was cooled to 0 C. The stirred mixture was then made basic to pH=14 by the dropwise addition of 10.0M NaOH, the organic layer was separated, and the aqueous phase was extracted with TBME (2*500 mL). The organic extracts were combined, dried over MgSO4, filtered and concentrated to a volume of 1 L. To this solution of free amine was added Boc2O or di-tert-butyldicarbonate (131 g, 0.600 mol) and the mixture stirred for 4 days at room temperature. Additional di-tert-butyldicarbonate (50 g, 0.23 mol) was added to the reaction and the mixture was refluxed for 3 hours and was then allowed cool to room temperature overnight. The reaction mixture was dried over MgSO4, filtered, and concentrated in vacuo to provide 80 g of crude material. This residue was purified by flash chromatography (2.5 kg of SiO2, eluted with 1% to 2% CH3OH/CH2Cl2) to provide 57 g (53%) of racemic N-Boc-(1R,2S)/(1S,2R)-1-amino-2-vinylcyclopropane carboxylic acid ethyl ester as a yellow oil which solidified while sitting in the refrigerator: 1H NMR (CDCl3, 300 MHz) δ 1.26 (t, J=7.1 Hz, 3H), 1.46 (s, 9H), 1.43-1.49 (m, 1H), 1.76-1.82 (br m, 1H), 2.14 (q, J=8.6 Hz, 1H), 4.18 (q, J=7.2 Hz, 2H), 5.12 (dd J=10.3, 1.7 Hz, 1H), 5.25 (br s, 1H), 5.29 (dd, J=17.6, 1.7 Hz, 1H), 5.77 (ddd, J=17.6, 10.3, 8.9 Hz, 1H); MS m/z 254.16 (M-1).
  • 33
  • [ 40682-54-0 ]
  • [ 102-96-5 ]
  • (2c,3t,4r,5c)-3,5-diphenyl-2-ethoxycarbonyl-4-nitro-pyrrolidine [ No CAS ]
  • 34
  • [ 2446-83-5 ]
  • [ 40682-54-0 ]
  • [ 1380335-44-3 ]
YieldReaction ConditionsOperation in experiment
51% With potassium carbonate; In tert-butyl methyl ether; at 40℃; for 6h;Air atmosphere; General procedure: To a solution of 1 (1.0 mmol) and 2 (2.0 mmol) in solvent (2.0 mL) was added base (20 mol %). The reaction was stirred at 40 oC until the reaction was completed which was monitored by TLC. The crude product was purified by column chromatography on silica gel (petroleum ether/EtOAc=25:1) to afford the pure 1,2,4-triazoline 3.
  • 35
  • [ 930-88-1 ]
  • [ 40682-54-0 ]
  • [ 1140972-10-6 ]
YieldReaction ConditionsOperation in experiment
81% With silver hexafluoroantimonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); triethylamine; In toluene; at 25℃; for 16h;Darkness; General procedure: A solution of the imino ester (1 mmol) and dipolarophile (1 mmol) in toluene (5 mL) was added to a suspension containing (R)- or (S)-Binap (0.05 mmol, 31 mg) and AgX (0.05 mmol) in toluene (5 mL). To the resulting suspension triethylamine (0.05 mmol, 7 μL) was added and the mixture was stirred at room temperature and in the absence of the light for 16-48 h (see main text). The precipitate was filtered and the complex was recovered. The organic filtrate was directly evaporated and the residue was purified by recrystallization or by flash chromatography yielding pure endo-cycloadducts.
  • 36
  • [ 941-69-5 ]
  • [ 40682-54-0 ]
  • [ 1443277-94-8 ]
YieldReaction ConditionsOperation in experiment
90% With C32H29FeN2OP; silver(I) acetate; triethylamine; In toluene; at -20℃; for 12h;Inert atmosphere; General procedure: AgOAc (2.5 mg, 0.015 mmol) and (Rc,Sp)-1b (9 mg, 0.0165 mmol) were stirred atroom temperature in 3 mL of toluene under nitrogen atmosphere for 1 h. The solutionwas cooled to -20 oC, and then added imino esters (0.5 mmol), N-phenylmaleimide(0.6 mmol) and Et3N (7.5μL, 0.05 mmol). The mixture was stirred at -20 for 12 h The residue was then purified by silica gel chromatography (hexanes/AcOEt, 2/1) toafford the cycloaddition product.
  • 38
  • [ 40682-54-0 ]
  • [ 17822-51-4 ]
  • (1R,3S,4R)-ethyl 8-oxo-1,4-diphenylhexahydro-1H-pyrazolo[1,2-a][1,2,4]triazine-3-carboxylate [ No CAS ]
  • 39
  • [ 40682-54-0 ]
  • [ 69624-88-0 ]
  • (1S,3R,4S)-ethyl 4-(3-bromophenyl)-8-oxo-1-phenylhexahydro-1H-pyrazolo[1,2-a][1,2,4]triazine-3-carboxylate [ No CAS ]
  • 40
  • [ 1173920-32-5 ]
  • [ 40682-54-0 ]
  • (1S,3R,4S)-ethyl 4-(4-bromophenyl)-8-oxo-1-phenylhexahydro-1H-pyrazolo[1,2-a][1,2,4]triazine-3-carboxylate [ No CAS ]
  • 41
  • [ 941-69-5 ]
  • [ 40682-54-0 ]
  • [ 2216-94-6 ]
  • C32H30N2O6 [ No CAS ]
  • 42
  • [ 40682-54-0 ]
  • [ 102-96-5 ]
  • (2R,3R,4S,5R)-ethyl 4-nitro-3,5-diphenylpyrrolidine-2-carboxylate [ No CAS ]
  • 43
  • [ 7559-36-6 ]
  • [ 40682-54-0 ]
  • (2R,3R,4S,5R)-ethyl-4 nitro-5-phenyl-3-p-tolylpyrrolidine-2-carboxylate [ No CAS ]
  • 44
  • [ 40682-54-0 ]
  • [ 4230-93-7 ]
  • (2R,3R,4S,5R)-ethyl 3-(3,4-dimethoxyphenyl)-4-nitro-5-phenylpyrrolidine-2-carboxylate [ No CAS ]
  • 45
  • [ 40682-54-0 ]
  • [ 70704-69-7 ]
  • (1S,3S,11bR)-ethyl 4,4-dicyano-3-phenyl-2,3,4,11b-tetrahydro-1H-pyrazino[2,1-a]phthalazine-1-carboxylate [ No CAS ]
  • 46
  • [ 40682-54-0 ]
  • icyano(6,7-dimethylphthalazin-2-ium-2-yl)methanide [ No CAS ]
  • (1S,3S,11bR)-ethyl 4,4-dicyano-9,10-dimethyl-3-phenyl-2,3,4,11b-tetrahydro-1H-pyrazino[2,1-a]phthalazine-1-carboxylate [ No CAS ]
  • 47
  • [ 40682-54-0 ]
  • [ 78032-08-3 ]
  • (1S,3S,11bR)-ethyl 4,4-dicyano-9,10-dimethyl-3-phenyl-2,3,4,11b-tetrahydro-1H-pyrazino[2,1-a]phthalazine-1-carboxylate [ No CAS ]
  • 48
  • [ 40682-54-0 ]
  • [ 94-41-7 ]
  • C26H25NO3 [ No CAS ]
  • ethyl 4-benzoyl-3,5-diphenylpyrrolidine-2-carboxylate [ No CAS ]
  • 49
  • [ 40682-54-0 ]
  • [ 1383003-35-7 ]
  • C24H25NO4 [ No CAS ]
  • C24H25NO4 [ No CAS ]
  • 50
  • [ 40682-54-0 ]
  • C14H14O2 [ No CAS ]
  • C25H27NO4 [ No CAS ]
  • C25H27NO4 [ No CAS ]
  • 51
  • [ 40682-54-0 ]
  • C15H16O2 [ No CAS ]
  • C26H29NO4 [ No CAS ]
  • C26H29NO4 [ No CAS ]
  • 52
  • [ 40682-54-0 ]
  • C13H11BrO2 [ No CAS ]
  • C24H24BrNO4 [ No CAS ]
  • C24H24BrNO4 [ No CAS ]
  • 53
  • [ 40682-54-0 ]
  • C14H14O3 [ No CAS ]
  • C25H27NO5 [ No CAS ]
  • C25H27NO5 [ No CAS ]
  • 54
  • [ 40682-54-0 ]
  • 2-(4-fluorobenzyl)-2-methylcyclopent-4-ene-1,3-dione [ No CAS ]
  • C24H24FNO4 [ No CAS ]
  • C24H24FNO4 [ No CAS ]
  • 55
  • [ 40682-54-0 ]
  • C16H18O2 [ No CAS ]
  • C27H31NO4 [ No CAS ]
  • C27H31NO4 [ No CAS ]
  • 56
  • [ 40682-54-0 ]
  • [ 1383003-36-8 ]
  • C28H27NO4 [ No CAS ]
  • C28H27NO4 [ No CAS ]
  • 57
  • [ 40682-54-0 ]
  • C14H11F3O2 [ No CAS ]
  • C25H24F3NO4 [ No CAS ]
  • C25H24F3NO4 [ No CAS ]
  • 58
  • [ 40682-54-0 ]
  • C13H11ClO2 [ No CAS ]
  • C24H24ClNO4 [ No CAS ]
  • C24H24ClNO4 [ No CAS ]
  • 59
  • [ 40682-54-0 ]
  • 2-Allyl-2-methyl-4-cyclopentene-1,3-dione [ No CAS ]
  • C20H23NO4 [ No CAS ]
  • C20H23NO4 [ No CAS ]
  • 60
  • [ 40682-54-0 ]
  • (E)-6-chloro-9-(2-tosylvinyl)-9H-purine [ No CAS ]
  • (2R,3R,4R,5R)-ethyl 3-(6-chloro-9H-purin-9-yl)-5-phenyl-4-tosylpyrrolidine-2-carboxylate [ No CAS ]
  • 61
  • [ 1204-35-9 ]
  • [ 40682-54-0 ]
  • (-)-ethyl 5-(3-chlorophenyl)-4,6-dioxo-3-phenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate [ No CAS ]
  • (+)-ethyl 5-(3-chlorophenyl)-4,6-dioxo-3-phenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2-((1R)-((tert-butylsulfinyl)amino)(phenyl)methyl)-6-(diphenylphosphanyl)-N,N-diisopropylbenzamide; water; silver fluoride; In toluene; at -20℃; for 10h; General procedure: 4.3. Typical procedure for the synthesis of 6 through thesilver-catalyzed [3+2] cycloaddtion of azomethine ylides4aen with N-aromatic maleimides 5a-h To the AgF (0. 8 mg, 0.0063 mmol, 2.5 mmol%) catalysis inreaction tube, 100 mLH2O was added to dissolve the AgF. Toluene(2 mL) was added and the resulting mixture was stirredfor 5 min. Then sys-(R, Rs)-2a (0.0082 g, 0.0138 mmol, 5.5 mmol%) was added. The mixture was stirred at 20 C for 15 min, theniminoester (0.6 mmol, 1.2 equiv) and maleimide (0.5 mmol,1.0 equiv) were added successively. The reaction was allowedto proceed for 10 h at 20 C, after which 5 mL H2O was addedto quench the reaction. The organic layer was diluted with 10 mLEtOAc and water layer was extracted with EtOAc (5mL2). The combined organic layer was dried with Na2SO4 and con-centrated. A portion of the cured was analysed with 1H NMR todetermine the diastereomeric ratio and recovered. The structuresof some products were known16 and conrmed by NMR, IR andMS. The enantiomeric excesses of the products were determinedby chiral stationary phase HPLC using a chiral column afterpurication.
  • 62
  • [ 20299-79-0 ]
  • [ 40682-54-0 ]
  • (-)-ethyl 4,6-dioxo-3-phenyl-5-(m-tolyl)octahydropyrrolo[3,4-c]pyrrole-1-carboxylate [ No CAS ]
  • (+)-ethyl 4,6-dioxo-3-phenyl-5-(m-tolyl)octahydropyrrolo[3,4-c]pyrrole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2-((1R)-((tert-butylsulfinyl)amino)(phenyl)methyl)-6-(diphenylphosphanyl)-N,N-diisopropylbenzamide; water; silver fluoride; In toluene; at -20℃; for 10h; General procedure: 4.3. Typical procedure for the synthesis of 6 through thesilver-catalyzed [3+2] cycloaddtion of azomethine ylides4aen with N-aromatic maleimides 5a-h To the AgF (0. 8 mg, 0.0063 mmol, 2.5 mmol%) catalysis inreaction tube, 100 mLH2O was added to dissolve the AgF. Toluene(2 mL) was added and the resulting mixture was stirredfor 5 min. Then sys-(R, Rs)-2a (0.0082 g, 0.0138 mmol, 5.5 mmol%) was added. The mixture was stirred at 20 C for 15 min, theniminoester (0.6 mmol, 1.2 equiv) and maleimide (0.5 mmol,1.0 equiv) were added successively. The reaction was allowedto proceed for 10 h at 20 C, after which 5 mL H2O was addedto quench the reaction. The organic layer was diluted with 10 mLEtOAc and water layer was extracted with EtOAc (5mL2). The combined organic layer was dried with Na2SO4 and con-centrated. A portion of the cured was analysed with 1H NMR todetermine the diastereomeric ratio and recovered. The structuresof some products were known16 and conrmed by NMR, IR andMS. The enantiomeric excesses of the products were determinedby chiral stationary phase HPLC using a chiral column afterpurication.
  • 63
  • [ 53534-14-8 ]
  • [ 40682-54-0 ]
  • (-)-ethyl 5-(3-bromophenyl)-4,6-dioxo-3-phenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate [ No CAS ]
  • (+)-ethyl 5-(3-bromophenyl)-4,6-dioxo-3-phenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2-((1R)-((tert-butylsulfinyl)amino)(phenyl)methyl)-6-(diphenylphosphanyl)-N,N-diisopropylbenzamide; water; silver fluoride; In toluene; at -20℃; for 10h; General procedure: 4.3. Typical procedure for the synthesis of 6 through thesilver-catalyzed [3+2] cycloaddtion of azomethine ylides4aen with N-aromatic maleimides 5a-h To the AgF (0. 8 mg, 0.0063 mmol, 2.5 mmol%) catalysis inreaction tube, 100 mLH2O was added to dissolve the AgF. Toluene(2 mL) was added and the resulting mixture was stirredfor 5 min. Then sys-(R, Rs)-2a (0.0082 g, 0.0138 mmol, 5.5 mmol%) was added. The mixture was stirred at 20 C for 15 min, theniminoester (0.6 mmol, 1.2 equiv) and maleimide (0.5 mmol,1.0 equiv) were added successively. The reaction was allowedto proceed for 10 h at 20 C, after which 5 mL H2O was addedto quench the reaction. The organic layer was diluted with 10 mLEtOAc and water layer was extracted with EtOAc (5mL2). The combined organic layer was dried with Na2SO4 and con-centrated. A portion of the cured was analysed with 1H NMR todetermine the diastereomeric ratio and recovered. The structuresof some products were known16 and conrmed by NMR, IR andMS. The enantiomeric excesses of the products were determinedby chiral stationary phase HPLC using a chiral column afterpurication.
  • 64
  • [ 19077-60-2 ]
  • [ 40682-54-0 ]
  • (-)-ethyl 5-(4-ethoxyphenyl)-4,6-dioxo-3-phenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate [ No CAS ]
  • (+)-ethyl 5-(4-ethoxyphenyl)-4,6-dioxo-3-phenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2-((1R)-((tert-butylsulfinyl)amino)(phenyl)methyl)-6-(diphenylphosphanyl)-N,N-diisopropylbenzamide; water; silver fluoride; In toluene; at -20℃; for 10h; General procedure: 4.3. Typical procedure for the synthesis of 6 through thesilver-catalyzed [3+2] cycloaddtion of azomethine ylides4aen with N-aromatic maleimides 5a-h To the AgF (0. 8 mg, 0.0063 mmol, 2.5 mmol%) catalysis inreaction tube, 100 mLH2O was added to dissolve the AgF. Toluene(2 mL) was added and the resulting mixture was stirredfor 5 min. Then sys-(R, Rs)-2a (0.0082 g, 0.0138 mmol, 5.5 mmol%) was added. The mixture was stirred at 20 C for 15 min, theniminoester (0.6 mmol, 1.2 equiv) and maleimide (0.5 mmol,1.0 equiv) were added successively. The reaction was allowedto proceed for 10 h at 20 C, after which 5 mL H2O was addedto quench the reaction. The organic layer was diluted with 10 mLEtOAc and water layer was extracted with EtOAc (5mL2). The combined organic layer was dried with Na2SO4 and con-centrated. A portion of the cured was analysed with 1H NMR todetermine the diastereomeric ratio and recovered. The structuresof some products were known16 and conrmed by NMR, IR andMS. The enantiomeric excesses of the products were determinedby chiral stationary phase HPLC using a chiral column afterpurication.
  • 65
  • [ 1081-17-0 ]
  • [ 40682-54-0 ]
  • (-)-ethyl 5-(4-methoxyphenyl)-4,6-dioxo-3-phenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate [ No CAS ]
  • (+)-ethyl 5-(4-methoxyphenyl)-4,6-dioxo-3-phenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2-((1R)-((tert-butylsulfinyl)amino)(phenyl)methyl)-6-(diphenylphosphanyl)-N,N-diisopropylbenzamide; water; silver fluoride; In toluene; at -20℃; for 10h; General procedure: 4.3. Typical procedure for the synthesis of 6 through thesilver-catalyzed [3+2] cycloaddtion of azomethine ylides4aen with N-aromatic maleimides 5a-h To the AgF (0. 8 mg, 0.0063 mmol, 2.5 mmol%) catalysis inreaction tube, 100 mLH2O was added to dissolve the AgF. Toluene(2 mL) was added and the resulting mixture was stirredfor 5 min. Then sys-(R, Rs)-2a (0.0082 g, 0.0138 mmol, 5.5 mmol%) was added. The mixture was stirred at 20 C for 15 min, theniminoester (0.6 mmol, 1.2 equiv) and maleimide (0.5 mmol,1.0 equiv) were added successively. The reaction was allowedto proceed for 10 h at 20 C, after which 5 mL H2O was addedto quench the reaction. The organic layer was diluted with 10 mLEtOAc and water layer was extracted with EtOAc (5mL2). The combined organic layer was dried with Na2SO4 and con-centrated. A portion of the cured was analysed with 1H NMR todetermine the diastereomeric ratio and recovered. The structuresof some products were known16 and conrmed by NMR, IR andMS. The enantiomeric excesses of the products were determinedby chiral stationary phase HPLC using a chiral column afterpurication.
  • 66
  • [ 821-06-7 ]
  • [ 24424-99-5 ]
  • [ 40682-54-0 ]
  • [ 681807-59-0 ]
YieldReaction ConditionsOperation in experiment
50% To a mixture of lithium tert-butoxide (17.60 g, 220 mmol) in toluene (250 mL) were added a solution of compound 2-3 (22.00 g, 117 mmol) in toluene (50 mL) and a solution of (E)-1,4-dibromobut-2-ene (20.00 g, 94 mmol) in toluene (50 mL) at 0C at the same time, the two solution was added at the same speed over 1 hour. The mixture was warmed to 30 C and stirred for 2 hours, and then quenched with water (200 mL). The resulting mixture was extracted with MTBE (200 mL). To the combined organic layers were added hydrochloric acid (1 M, 200 mL), the mixture was stirred for 2 hours. The seperated organic layer was extracted with water (150 mL). To the water layer was added sodium chloride (131.00 g, 2241 mmol) and MTBE (200 mL). The mixture was adjusted with aqueous NaOH solution (10 M) to pH between 12 and 13. The organic layer was separated; the water layer was extracted with MTBE (100 mL). To the combined organic layers was added Boc2O (21 mL, 98 mmol). The mixture was stirred at rt overnight and then warmed to 60 C, further stirred for 2 hours. The mixture was cooled to rt and dried over anhydrous Na2504, and then concentrated in vavuo. The residue was purified by silica gel column chromatography eluted with PE : EtOAc (V: V) = 5 : 1 to afford compound 2-4 (12g, 50%) as yellow oil. 1H NIVIR (400 MHz, CDC13): (5 5.17-5.80 (m, 1H), 5.29 (s, 1H), 5.06-5.09 (m, 1H),4.12-4.19 (m, 2H), 2.17-2.14 (m, 1H), 1.77 (s, 1H), 1.43 (s, 1H), 1.41 (s, 9H), 1.24 (t, J= 7.2 Hz, 3H) ppm.
  • 67
  • [ 21778-81-4 ]
  • [ 40682-54-0 ]
  • C21H20N2O3 [ No CAS ]
  • 68
  • [ 1463-60-1 ]
  • [ 40682-54-0 ]
  • C21H20N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 20℃; for 10h; Molecular sieve;
  • 69
  • [ 53590-50-4 ]
  • [ 40682-54-0 ]
  • C20H17BrN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 20℃; for 10h; Molecular sieve;
  • 70
  • [ 40682-54-0 ]
  • C9H6F3NO2 [ No CAS ]
  • (2R,3R,4S,5R)-ethyl 4-nitro-3,5-diphenyl-3-(trifluoromethyl)pyrrolidine-2-carboxylate [ No CAS ]
  • 71
  • [ 40682-54-0 ]
  • [ 343830-62-6 ]
  • ethyl (2'S,3R,4'S,5'S)-1-benzyl-2-oxo-2',4'-diphenylspiro[indoline-3,3'-pyrrolidine]-5'-carboxylate [ No CAS ]
  • 72
  • [ 40682-54-0 ]
  • [ 623-91-6 ]
  • C19H25NO6 [ No CAS ]
  • C19H25NO6 [ No CAS ]
  • C19H25NO6 [ No CAS ]
  • C19H25NO6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(acetonitrile)copper(I) perchlorate; siloxane-FOXAP; potassium carbonate; In dichloromethane; at 20℃;Inert atmosphere; Schlenk technique; Molecular sieve; General procedure: Cu(OAc)2·H2O (0.04 mmol) and the ferrocenyl-oxazoline ligand L1(0.04 mmol) were added under argon to a 10 mL Schlenk tube, containing activated 4Å MS. The freshly distilled anhydrous DCM (2 mL) was added into the tube. After being stirred for 60 min at room temperature, the solution was cooled to 0 oC before the glycine imino ester 1 (0.8 mmol), maleate ester 2b-c (1.2 mmol) and Et3N (0.08 mmol) were added subsequently. The reaction mixture was stirred at -5 oC for overnight. When the reaction was complete as monitored by TLC, the pure adducts was purified by column chromatography on silica gel (200- 300 mesh). Enantiomeric excess was determined by chiral HPLC: racemate of all products for HPLC analyses were prepared by using Cu(OAc)2·H2O/PPh3.
With tetrakis(acetonitrile)copper(I) perchlorate; siloxane-FOXAP; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20℃;Inert atmosphere; Schlenk technique; Molecular sieve; General procedure: Cu(OAc)2·H2O (0.04 mmol) and the ferrocenyl-oxazoline ligand L1(0.04 mmol) were added under argon to a 10 mL Schlenk tube, containing activated 4Å MS. The freshly distilled anhydrous DCM (2 mL) was added into the tube. After being stirred for 60 min at room temperature, the solution was cooled to 0 oC before the glycine imino ester 1 (0.8 mmol), maleate ester 2b-c (1.2 mmol) and Et3N (0.08 mmol) were added subsequently. The reaction mixture was stirred at -5 oC for overnight. When the reaction was complete as monitored by TLC, the pure adducts was purified by column chromatography on silica gel (200- 300 mesh). Enantiomeric excess was determined by chiral HPLC: racemate of all products for HPLC analyses were prepared by using Cu(OAc)2·H2O/PPh3.
  • 73
  • [ 40682-54-0 ]
  • [ 623-91-6 ]
  • C19H25NO6 [ No CAS ]
  • C19H25NO6 [ No CAS ]
  • C19H25NO6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(acetonitrile)copper(I) perchlorate; siloxane-FOXAP; caesium carbonate; In dichloromethane; at -5℃;Inert atmosphere; Schlenk technique; Molecular sieve; General procedure: Cu(OAc)2·H2O (0.04 mmol) and the ferrocenyl-oxazoline ligand L1(0.04 mmol) were added under argon to a 10 mL Schlenk tube, containing activated 4Å MS. The freshly distilled anhydrous DCM (2 mL) was added into the tube. After being stirred for 60 min at room temperature, the solution was cooled to 0 oC before the glycine imino ester 1 (0.8 mmol), maleate ester 2b-c (1.2 mmol) and Et3N (0.08 mmol) were added subsequently. The reaction mixture was stirred at -5 oC for overnight. When the reaction was complete as monitored by TLC, the pure adducts was purified by column chromatography on silica gel (200- 300 mesh). Enantiomeric excess was determined by chiral HPLC: racemate of all products for HPLC analyses were prepared by using Cu(OAc)2·H2O/PPh3.
  • 74
  • [ 40682-54-0 ]
  • [ 623-91-6 ]
  • C19H25NO6 [ No CAS ]
  • C19H25NO6 [ No CAS ]
  • C19H25NO6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With siloxane-FOXAP; copper(II) acetate monohydrate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃;Inert atmosphere; Schlenk technique; Molecular sieve; General procedure: Cu(OAc)2·H2O (0.04 mmol) and the ferrocenyl-oxazoline ligand L1(0.04 mmol) were added under argon to a 10 mL Schlenk tube, containing activated 4Å MS. The freshly distilled anhydrous DCM (2 mL) was added into the tube. After being stirred for 60 min at room temperature, the solution was cooled to 0 oC before the glycine imino ester 1 (0.8 mmol), maleate ester 2b-c (1.2 mmol) and Et3N (0.08 mmol) were added subsequently. The reaction mixture was stirred at -5 oC for overnight. When the reaction was complete as monitored by TLC, the pure adducts was purified by column chromatography on silica gel (200- 300 mesh). Enantiomeric excess was determined by chiral HPLC: racemate of all products for HPLC analyses were prepared by using Cu(OAc)2·H2O/PPh3.
  • 75
  • [ 40682-54-0 ]
  • [ 624-48-6 ]
  • 2-ethyl 3,4-dimethyl 5-phenylpyrrolidine-2,3,4-tricarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With copper(II) acetate monohydrate; triphenylphosphine; In dichloromethane; at -5℃;Inert atmosphere; Schlenk technique; Molecular sieve; (2R,3R,4S,5S)-2-ethyl 3,4-dimethyl phenylpyrrolidine-2,3,4-tricarboxylate (4nc) Ligh yellow oil: Yield = 65%; ee = 92.4%; 1H NMR (500 MHz, CDCl3) δ 7.45 (d, J = 7.3 Hz, 2H), 7.31 (t, J = 7.5 Hz, 2H), 7.25 (d, J = 7.3 Hz, 1H), 4.66 (s, 1H), 4.34 (d, J = 1.9 Hz, 1H), 4.24 (qd, J = 7.1, 2.8 Hz, 2H), 3.70 (s, 3H), 3.63 (s, 3H), 3.62-3.58 (m, 1H), 3.24 (t, J = 8.3 Hz, 1H), 2.78 (br, 1H), 1.30 (t, J = 7.1 Hz, 3H). 13C NMR (126 MHz, CDCl3) δ 172.48, 171.61, 141.31, 128.52, 127.76, 126.96, 64.51, 62.01, 61.53, 54.33, 52.38, 52.09, 49.92, 14.16. (KBr) υ 2982, 1732, 1440, 1370, 1265, 1170, 910, 715 cm-1. HRMS Calcd. For C17H22NO6+ [M+H]+:336.1444; found: 336.1428. HPLC (Chiralpak AD-H column, hexane/2-propanol = 90/10, flow rate = 1 mL/min) tR = 11.90 min, 19.93 min.
  • 76
  • [ 40682-54-0 ]
  • [ 624-48-6 ]
  • 2-ethyl 3,4-dimethyl (2R,3R,4S,5S)-5-phenylpyrrolidine-2,3,4-tricarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With siloxane-FOXAP; copper(II) acetate monohydrate; triethylamine; In dichloromethane; at -5℃;Inert atmosphere; Schlenk technique; Molecular sieve; (2R,3R,4S,5S)-2-ethyl 3,4-dimethyl phenylpyrrolidine-2,3,4-tricarboxylate (4nc) Ligh yellow oil: Yield = 65%; ee = 92.4%; 1H NMR (500 MHz, CDCl3) δ 7.45 (d, J = 7.3 Hz, 2H), 7.31 (t, J = 7.5 Hz, 2H), 7.25 (d, J = 7.3 Hz, 1H), 4.66 (s, 1H), 4.34 (d, J = 1.9 Hz, 1H), 4.24 (qd, J = 7.1, 2.8 Hz, 2H), 3.70 (s, 3H), 3.63 (s, 3H), 3.62-3.58 (m, 1H), 3.24 (t, J = 8.3 Hz, 1H), 2.78 (br, 1H), 1.30 (t, J = 7.1 Hz, 3H). 13C NMR (126 MHz, CDCl3) δ 172.48, 171.61, 141.31, 128.52, 127.76, 126.96, 64.51, 62.01, 61.53, 54.33, 52.38, 52.09, 49.92, 14.16. (KBr) υ 2982, 1732, 1440, 1370, 1265, 1170, 910, 715 cm-1. HRMS Calcd. For C17H22NO6+ [M+H]+:336.1444; found: 336.1428. HPLC (Chiralpak AD-H column, hexane/2-propanol = 90/10, flow rate = 1 mL/min) tR = 11.90 min, 19.93 min.
  • 77
  • [ 40682-54-0 ]
  • ethyl (2R,4S,5S)-1-(2-ethoxy-2-oxoethyl)-2,5-diphenylimidazolidine-4-carboxylate [ No CAS ]
  • 78
  • [ 40682-54-0 ]
  • [ 1402043-13-3 ]
  • [ 16836-95-6 ]
  • ethyl(2S,4S,5S)-3-(2-chloro-6-((4-methylphenyl)sulfonamido)benzyl)-1-(2-ethoxy-2-oxoethyl)-2,5-diphenylimidazolidine-4-carboxylate [ No CAS ]
  • 79
  • [ 40682-54-0 ]
  • C14H13ClFNO2S [ No CAS ]
  • [ 16836-95-6 ]
  • ethyl(2S,4S,5S)-1-(2-ethoxy-2-oxoethyl)-3-(2-fluoro-6-((4-methylphenyl)sulfonamido)benzyl)-2,5-diphenylimidazolidine-4-carboxylate [ No CAS ]
  • 80
  • [ 40682-54-0 ]
  • C14H13ClFNO2S [ No CAS ]
  • [ 16836-95-6 ]
  • ethyl(2S,4S,5S)-1-(2-ethoxy-2-oxoethyl)-3-(5-fluoro-2-((4-methylphenyl)sulfonamido)benzyl)-2,5-diphenylimidazolidine-4-carboxylate [ No CAS ]
  • 81
  • [ 40682-54-0 ]
  • C14H13ClFNO2S [ No CAS ]
  • [ 16836-95-6 ]
  • ethyl(2S,4S,5S)-1-(2-ethoxy-2-oxoethyl)-3-(4-fluoro-2-((4-methylphenyl)sulfonamido)benzyl)-2,5-diphenylimidazolidine-4-carboxylate [ No CAS ]
  • 82
  • [ 40682-54-0 ]
  • C15H16ClNO2S [ No CAS ]
  • [ 16836-95-6 ]
  • ethyl(2S,4S,5S)-1-(2-ethoxy-2-oxoethyl)-3-(2-methyl-6-((4-methylphenyl)sulfonamido)benzyl)-2,5-diphenylimidazolidine-4-carboxylate [ No CAS ]
  • 83
  • [ 895578-39-9 ]
  • [ 40682-54-0 ]
  • [ 16836-95-6 ]
  • ethyl(2S,4S,5S)-1-(2-ethoxy-2-oxoethyl)-3-(5-methyl-2-((4-methylphenyl)sulfonamido)benzyl)-2,5-diphenylimidazolidine-4-carboxylate [ No CAS ]
  • 84
  • [ 40682-54-0 ]
  • N-(2-(chloromethyl)-5-methylphenyl)-4-methylbenzenesulfonamide [ No CAS ]
  • [ 16836-95-6 ]
  • ethyl(2S,4S,5S)-1-(2-ethoxy-2-oxoethyl)-3-(4-methyl-2-((4-methylphenyl)sulfonamido)benzyl)-2,5-diphenylimidazolidine-4-carboxylate [ No CAS ]
  • 85
  • [ 895578-41-3 ]
  • [ 40682-54-0 ]
  • [ 16836-95-6 ]
  • ethyl(2S,4S,5S)-1-(2-ethoxy-2-oxoethyl)-3-(3-methyl-2-((4-methylphenyl)sulfonamido)benzyl)-2,5-diphenylimidazolidine-4-carboxylate [ No CAS ]
Same Skeleton Products
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