147959-19-1|(S)-tert-Butyl 2,2-dimethyl-4-(2-oxoethyl)oxazolidine-3-carboxylate| Ambeed

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Quality Control of [ 147959-19-1 ] Purity: 95% SDS Specification

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Product Details of [ 147959-19-1 ]

CAS No. :	147959-19-1
Formula :	C₁₂H₂₁NO₄
M.W :	243.30
SMILES Code :	CC(C)(C)OC(=O)N1[C@@H](CC=O)COC1(C)C
MDL No. :	MFCD08234426
InChI Key :	GAWRNYMYEGSVFV-VIFPVBQESA-N
Pubchem ID :	10586317

Safety of [ 147959-19-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of [ 147959-19-1 ]

* 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 [ 147959-19-1 ]

[ 147959-19-1 ] Synthesis Path-Downstream 1~35

1
[ 147959-18-0 ]
[ 147959-19-1 ]

Yield	Reaction Conditions	Operation in experiment
100%		Example 92 (S)-2-[4-(2,3-Dichloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-3-(tetrahydro-pyran-2-yl)-propionamide (S)-4-(2-Hydroxy-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid t-butyl ester was prepared according to the literature procedure (J. Org. Chem. 2001, 66, 206-215). A solution of dimethylsulfoxide (3.5 mL) in dichloromethane (15 mL) was added dropwise to a cooled solution (-78 C.) of oxalyl chloride (2M in dichloromethane, 13 mL) in dichloromethane (40 mL). The solution was stirred at -60 C. for 15 min before the slow addition of (S)-4-(2-hydroxy-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid t-butyl ester (4.5 g, 18.37 mmol) in dichloromethane (20 mL). The mixture was stirred at -60 C. for 30 min and triethylamine (13 mL) was added. After stirring for 30 min, the cooling bath was removed and the mixture was stirred for 1 h at room temperature. The mixture was extracted with dichloromethane and water. The organic layer was dried over sodium sulfate. Solvents were evaporated to give (S)-2,2-dimethyl-4-(2-oxo-ethyl)-oxazolidine-3-carboxylic acid t-butyl ester (4.50 g, 100%) as a colorless oil: 1H NMR (300 MHz, CDCl3) delta ppm 1.42-1.52 (m, 12H), 1.51, 1.63 (2*s, 3H), 2.50-3.16 (m, 2H), 3.73 (d, J=9.1 Hz, 1H), 3.99-4.16 (m, 1H), 4.22-4.44 (m, 1H), 9.79 (s, 1H).
97%		A solution of DMSO (5.3 mL, 74.5 mmol) in CH2Cl2 (23 mL) was added dropwise to a cooled solution (-60 C) of oxalyl chloride (3.44 mL, 40.0 mmol) in CH2Cl2 (83 mL). The solution was stirred for 15 min at -60 C, before a solution of alcohol 9 (7.017 g, 28.6 mmol) in CH2Cl2 (36 mL, including rinses) was added slowly. After stirring at -60 0C for 30 min, Et3N (19.9 mL, 142.8 mmol) was added. After 30 min, the cold bath was removed and the reaction was stirred an additional hour at room temperature. The mixture was poured into H2O (360 mL) and extracted with CH2Cl2 (5 x 100 mL). The combined organic layers were washed with H2O (180 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel («-hexane/Et2O 1 :1) to afford 6 (6.72O g, 97%) as a colorless solid: mp 34-38 C lit.4 < 40 C; [alpha]22D +35.1 (c l .03, CHCl3) lit.36 [alpha]22D +34.0 (c l.O, CHCl3); 1H NMR (400 MHz, C2D2Cl4, 120 0C): delta 1.47 (s, 9 H), 1.49 (s, 3 H), 1.56 (s, 3 H), 2.63 (dd, J- 7.7, 16.6 Hz, 1 H), 2.88 (dd, J = 4.0, 16.6 Hz, 1 H), 3.70 (bd, J= 9.2 Hz, 1 H), 4.05 (dd, J= 6.0, 9.2 Hz, 1 H), 4.24-4.33 (m, 1 H), 9.77 (bs, 1 H); 13C NMR (100 MHz, C2D2Cl4, 120 0C): delta 24.3 (CH3), 27.1 (CH3), 28.5 (CH3), 48.0 (CH2), 52.8 (CH), 67.8 (CH2), 80.4 (C), 93.9 (C), 151.8 (C), 199.9 (CH).
		A solution of DMSO (3.57 mL, 46.2 mmol) in dry dichloromethane (13 mL) was added to a solution of oxalyl chloride (1.83 mL, 20.0 mmol) in dry dichloromethane (50 mL) at -78 C. The reaction mixture was stirred for 15 min at -78 C and a solution of 8 (3.43 g, 14.0 mmol) in dichloromethane (30 mL) was added. The reaction mixture was stirred for another 45 min at -60 C. Next, Et3N (13.3 mL, 95.2 mmol) was then added at -78 C, the cooling bath removed, and the reaction mixture was stirred for 1 h at room temperature. The reaction was quenched by the addition of water and the aqueous phase was extracted with dichloromethane. The combined organic extracts were washed successively with water, aqueous NaHCO3 and brine, dried with Na2SO4, filtered through Celite, and the solvent was removed in vacuo to give the crude aldehyde as a pale yellow oil. This aldehyde was used without any purification for the next step.

		At first, DMSO (1.3 mL, 18 mmol) was added to a stirred solution of oxalyl chloride (0.8 mL, 9 mmol), in dry CH2Cl2 (25 mL) at -78 C and stirred at the same temperature for 30 min. A solution of 6 (2.0 g, 8.1 mmol) in dry CH2Cl2 (10 mL) was added at -78 C to the reaction mixture and stirred for 1 h at the same temperature. Next, Et3N (6.8 mL, 49 mmol) was added at -78 C and then stirred for an additional 30 min at rt. The reaction mixture was diluted with water (15 mL) and extracted with dichloromethane (2 × 50 mL). The combined organic layers were washed with brine (50 mL), dried over Na2SO4 and concentrated to obtain the aldehyde as a pale yellow syrup. The aldehyde was used for the next reaction without further purification.
	With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 18℃; for 2.1h;Schlenk technique;	Step 2: (5)-tert-butyl 2,2-dimethyl-4-(2-oxoethyl)oxazolidine-3 -carboxylateTo a solution of DMSO (1.591 mL, 22.42 mmol) in dry DCM (15 mL) at -78C was added dropwise oxalyl chloride (1.366 g, 10.76 mmol) in a schlenk tube and stirred for 30 mm. A solution of (5)-tert-butyl 4-(2-hydroxyethyl)-2,2-dimethyloxazolidine-3 -carboxylate (2.2 g, 8.97mmol) in 25 mL of DCM was added dropwise. After further stirring at -78C for 30 mi Et3N (7.50 mL, 53.8 mmol) was added dropwise, and then the mixture was warmed to 18C and stirred for 1.6 h. TLC showed the reaction was complete. The mixture was diluted with water (50 mL) and extracted with DCM (60 mL x 3). The combined organic layers were washed with water (50 mL) and brine (40 mL), dried over anhydrous sodium sulfate, filtered and concentratedto give the title compound.
6.06 g	With sulfur trioxide pyridine complex; triethylamine; In dimethyl sulfoxide; at 20℃; for 1h;	Process obtained in a 3 (S)-tert-butyl 4 - (2-hydroxyethyl) - 2,2-dimethyl-3-carboxylate (5.94g) [...] DMSO (59.4 ml) of triethylamine solution (16.9 ml) and trioxide pyridine complex (12.56g) and added in ambient temperature, copper at a temperature 1 time stirring section. Implanted water sodium bicarbonate saturation reaction mixture, extracted to ethyl acetic acid. Dry magnesium sulfate anhydride organic layer, after filtration, was concentrating. Obtained residue silica gel chromatography (developing solvent: hexane/acetic acid ethyl) for purifying the, title compound 6.06g is obtained.

References: [1]Patent: US2009/264445,2009,A1 .Location in patent: Page/Page column 73.
[2]Chemistry - A European Journal,2017,vol. 23,p. 6654 - 6662.
[3]Organic Letters,2005,vol. 7,p. 1423 - 1426.
[4]Patent: WO2006/94770,2006,A2 .Location in patent: Page/Page column 8; 16.
[5]Journal of Organic Chemistry,2004,vol. 69,p. 5023 - 5036.
[6]Journal of Medicinal Chemistry,1997,vol. 40,p. 495 - 505.
[7]Chemical and Pharmaceutical Bulletin,1997,vol. 45,p. 2116 - 2118.
[8]Synlett,2006,p. 1181 - 1184.
[9]Tetrahedron Asymmetry,2011,vol. 22,p. 1234 - 1238.
[10]Tetrahedron Asymmetry,2011,vol. 22,p. 1855 - 1860.
[11]Chemistry - An Asian Journal,2015,vol. 10,p. 474 - 482.
[12]Patent: WO2015/164308,2015,A1 .Location in patent: Page/Page column 71.
[13]Patent: KR2016/43114,2016,A .Location in patent: Paragraph 0602-0604.

2
[3-(3-Bromo-phenyl)-propyl]-triphenyl-phosphonium; iodide [ No CAS ]
[ 147959-19-1 ]
(S)-4-[(E)-5-(3-Bromo-phenyl)-pent-2-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 506 - 514.

3
[3-(2-Bromo-phenyl)-propyl]-triphenyl-phosphonium; iodide [ No CAS ]
[ 147959-19-1 ]
(S)-4-[(E)-5-(2-Bromo-phenyl)-pent-2-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 495 - 505.

4
[ 25791-20-2 ]
[ 147959-19-1 ]
(S)-4-((Z)-Hexadec-2-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1997,vol. 45,p. 2116 - 2118.

5
[ 21204-67-1 ]
[ 147959-19-1 ]
(S)-4-((E)-3-Methoxycarbonyl-allyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1997,vol. 45,p. 2116 - 2118.

6
[ 558-13-4 ]
[ 147959-19-1 ]
4-(3,3-dibromo-allyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Bioorganic and medicinal chemistry letters,2004,vol. 14,p. 275 - 278.

7
[ 1694-31-1 ]
[ 14205-43-7 ]
[ 147959-19-1 ]
[ 596828-12-5 ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 6172 - 6183.

8
[ 35059-50-8 ]
[ 147959-19-1 ]
(4S)-4-(3'-tert-butoxycarbonyl-2-oxopropyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 6172 - 6183.

9
[ 141-97-9 ]
[ 57-13-6 ]
[ 147959-19-1 ]
(4S,4''S)-4-(3''-tert-butoxycarbonyl-2'',2''-dimethyloxazolidin-4''-ylmethyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester [ No CAS ]
(4R,4''S)-4-(3''-tert-butoxycarbonyl-2'',2''-dimethyloxazolidin-4''-ylmethyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester [ No CAS ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 6172 - 6183.

10
[ 105-45-3 ]
[ 147959-19-1 ]
[ 14205-39-1 ]
[ 596828-11-4 ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 6172 - 6183.

11
[ 90965-06-3 ]
[ 147959-19-1 ]
[ 151139-90-1 ]

References: [1]Organic Letters,2004,vol. 6,p. 2929 - 2932.

12
[ 147959-19-1 ]
(2,6-anhydro-3,4,5-tri-O-benzyl-1,7-dideoxy-L-glycero-D-gluco-heptitol-1-yl)triphenylphosphonium iodide [ No CAS ]
[ 740817-05-4 ]

References: [1]Journal of Organic Chemistry,2004,vol. 69,p. 5023 - 5036.

13
[ 75-52-5 ]
[ 80522-42-5 ]
[ 147959-19-1 ]
4-(3-amino-2-triisopropylsilanyloxy-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester [ No CAS ]

References: [1]Organic Letters,2005,vol. 7,p. 1423 - 1426.
[2]Organic Letters,2005,vol. 7,p. 1423 - 1426.

14
[ 75-52-5 ]
[ 80522-42-5 ]
[ 147959-19-1 ]
(4S)-2,2-dimethyl-4-[(2S)-2-triisopropylsilanyloxy-3-nitropropyl]oxazolidine-3-carboxylic acid tert-butyl ester [ No CAS ]
[ 850996-91-7 ]

References: [1]Organic Letters,2005,vol. 7,p. 1423 - 1426.
[2]Organic Letters,2005,vol. 7,p. 1423 - 1426.

15
[ 75-52-5 ]
[ 147959-19-1 ]
(4S)-4-[(2S)-2-hydroxy-3-nitropropyl]-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester [ No CAS ]
[ 850996-88-2 ]

Yield	Reaction Conditions	Operation in experiment
	lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃;Product distribution / selectivity;	With key building block 6 in hand, its nitroaldol (Henry) reaction with nitromethane was examined (Table 1). LiAlH418- TBAF19- as well as t-BuOK20-catalyzed Henry reactions led to nitro alcohols 12 and 13 with low diastereoselectivity, reflecting that the existing stereogenic center is too far away from the newly created one to exert appreciable asymmetric induction (Table 1, entries 1-3).21 An obvious way of resolving this problem was the introduction of additional chiral information, i.e. application of a chiral catalyst. In fact double stereodifferentiation using Shibasaki's well established heterobimetallic (,S)-BINOL catalyst 1422 (5 mol%, THF, -40 C, 3 d) led to 12 with high diastereoselectivity albeit in low yield (Table 1, entry 4).Recently, other highly efficient chiral catalysts for asymmetric Henry reactions have been developed. Thus, Corey23 and Maruoka24 have utilized chiral quaternary ammonium fluorides as catalysts while Trost25 has presented a dinuclear zinc catalyst. Salen-cobalt(II) complexes have been used by Yamada whereas J°rgensen and Evans have introduced bis(oxazoline)-coprhoer(II) complexes. The latter seemed to be the catalysts of choice, at least for aliphatic aldehydes, with respect to attainable yields and degree of stereoselectivity. EPO <DP n="10"/>Table 1. Diastereoselective Henry Reaction of Aldehyde 6 with Nitromethaneyield ratio0 entry catalyst conditions(%)a 12:131 LiAlH4 THF, rt 53 56:442 TBAF THF, rt 33 43:573 r-BuOK t- 72 23:77BuOH/THF,00C4 14 THF, -40 C 45 98:25 {Cu[(+> EtOH, rt 87 92:815] (OAc)26 (CuK-)- EtOH, rt 85 9:9115](OAc)27 {Cu[(+> EtOH, rt 94 97:316](OAc)28 (Cu[(-)- EtOH, rt 91 8:9216I)(OAc)2a isolated yield b determined by HPLC analysis of crude reaction mixtures EPO <DP n="11"/>Indeed application of Evans' bis(oxazoline) copper(II) acetate-based catalysts {Cu[(+)- 15](OAc)2 and in particular {Cu[(+)-16](OAc)2 (5 mol%, EtOH, rt, 5 d) gave the desired nitro alcohol 12 both with high diastereoselectivity and in high yield (Table 1 , entries 5 and 7). Finally, to obtain selectively diastereomer 13, aldehyde 6 was reacted with nitromethane in the presence of the enantiomeric catalysts {Cu[(-)-15](OAc)2 and {Cu[(-)-16] (OAc)2 respectively. In these cases slightly lower stereoselectivities and yields were observed reflecting a mismatched pairing (Table 1, entries 6 and 8).
	potassium tert-butylate; In tetrahydrofuran; tert-butyl alcohol; at 0℃;Product distribution / selectivity;	With key building block 6 in hand, its nitroaldol (Henry) reaction with nitromethane was examined (Table 1). LiAlH418- TBAF19- as well as t-BuOK20-catalyzed Henry reactions led to nitro alcohols 12 and 13 with low diastereoselectivity, reflecting that the existing stereogenic center is too far away from the newly created one to exert appreciable asymmetric induction (Table 1, entries 1-3).21 An obvious way of resolving this problem was the introduction of additional chiral information, i.e. application of a chiral catalyst. In fact double stereodifferentiation using Shibasaki's well established heterobimetallic (,S)-BINOL catalyst 1422 (5 mol%, THF, -40 C, 3 d) led to 12 with high diastereoselectivity albeit in low yield (Table 1, entry 4).Recently, other highly efficient chiral catalysts for asymmetric Henry reactions have been developed. Thus, Corey23 and Maruoka24 have utilized chiral quaternary ammonium fluorides as catalysts while Trost25 has presented a dinuclear zinc catalyst. Salen-cobalt(II) complexes have been used by Yamada whereas J°rgensen and Evans have introduced bis(oxazoline)-coprhoer(II) complexes. The latter seemed to be the catalysts of choice, at least for aliphatic aldehydes, with respect to attainable yields and degree of stereoselectivity. EPO <DP n="10"/>Table 1. Diastereoselective Henry Reaction of Aldehyde 6 with Nitromethaneyield ratio0 entry catalyst conditions(%)a 12:131 LiAlH4 THF, rt 53 56:442 TBAF THF, rt 33 43:573 r-BuOK t- 72 23:77BuOH/THF,00C4 14 THF, -40 C 45 98:25 {Cu[(+> EtOH, rt 87 92:815] (OAc)26 (CuK-)- EtOH, rt 85 9:9115](OAc)27 {Cu[(+> EtOH, rt 94 97:316](OAc)28 (Cu[(-)- EtOH, rt 91 8:9216I)(OAc)2a isolated yield b determined by HPLC analysis of crude reaction mixtures EPO <DP n="11"/>Indeed application of Evans' bis(oxazoline) copper(II) acetate-based catalysts {Cu[(+)- 15](OAc)2 and in particular {Cu[(+)-16](OAc)2 (5 mol%, EtOH, rt, 5 d) gave the desired nitro alcohol 12 both with high diastereoselectivity and in high yield (Table 1 , entries 5 and 7). Finally, to obtain selectively diastereomer 13, aldehyde 6 was reacted with nitromethane in the presence of the enantiomeric catalysts {Cu[(-)-15](OAc)2 and {Cu[(-)-16] (OAc)2 respectively. In these cases slightly lower stereoselectivities and yields were observed reflecting a mismatched pairing (Table 1, entries 6 and 8).
	tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20℃;Product distribution / selectivity;	With key building block 6 in hand, its nitroaldol (Henry) reaction with nitromethane was examined (Table 1). LiAlH418- TBAF19- as well as t-BuOK20-catalyzed Henry reactions led to nitro alcohols 12 and 13 with low diastereoselectivity, reflecting that the existing stereogenic center is too far away from the newly created one to exert appreciable asymmetric induction (Table 1, entries 1-3).21 An obvious way of resolving this problem was the introduction of additional chiral information, i.e. application of a chiral catalyst. In fact double stereodifferentiation using Shibasaki's well established heterobimetallic (,S)-BINOL catalyst 1422 (5 mol%, THF, -40 C, 3 d) led to 12 with high diastereoselectivity albeit in low yield (Table 1, entry 4).Recently, other highly efficient chiral catalysts for asymmetric Henry reactions have been developed. Thus, Corey23 and Maruoka24 have utilized chiral quaternary ammonium fluorides as catalysts while Trost25 has presented a dinuclear zinc catalyst. Salen-cobalt(II) complexes have been used by Yamada whereas J°rgensen and Evans have introduced bis(oxazoline)-coprhoer(II) complexes. The latter seemed to be the catalysts of choice, at least for aliphatic aldehydes, with respect to attainable yields and degree of stereoselectivity. EPO <DP n="10"/>Table 1. Diastereoselective Henry Reaction of Aldehyde 6 with Nitromethaneyield ratio0 entry catalyst conditions(%)a 12:131 LiAlH4 THF, rt 53 56:442 TBAF THF, rt 33 43:573 r-BuOK t- 72 23:77BuOH/THF,00C4 14 THF, -40 C 45 98:25 {Cu[(+> EtOH, rt 87 92:815] (OAc)26 (CuK-)- EtOH, rt 85 9:9115](OAc)27 {Cu[(+> EtOH, rt 94 97:316](OAc)28 (Cu[(-)- EtOH, rt 91 8:9216I)(OAc)2a isolated yield b determined by HPLC analysis of crude reaction mixtures EPO <DP n="11"/>Indeed application of Evans' bis(oxazoline) copper(II) acetate-based catalysts {Cu[(+)- 15](OAc)2 and in particular {Cu[(+)-16](OAc)2 (5 mol%, EtOH, rt, 5 d) gave the desired nitro alcohol 12 both with high diastereoselectivity and in high yield (Table 1 , entries 5 and 7). Finally, to obtain selectively diastereomer 13, aldehyde 6 was reacted with nitromethane in the presence of the enantiomeric catalysts {Cu[(-)-15](OAc)2 and {Cu[(-)-16] (OAc)2 respectively. In these cases slightly lower stereoselectivities and yields were observed reflecting a mismatched pairing (Table 1, entries 6 and 8).

References: [1]Organic Letters,2005,vol. 7,p. 1423 - 1426.
[2]Organic Letters,2005,vol. 7,p. 1423 - 1426.
[3]Patent: WO2006/94770,2006,A2 .Location in patent: Page/Page column 8-10.
[4]Patent: WO2006/94770,2006,A2 .Location in patent: Page/Page column 8-10.
[5]Patent: WO2006/94770,2006,A2 .Location in patent: Page/Page column 8-10.

16
[ 1779-49-3 ]
[ 147959-19-1 ]
[ 860264-38-6 ]

Yield	Reaction Conditions	Operation in experiment
74%	With n-butyllithium; In tetrahydrofuran; hexane; at 0 - 20℃; for 4.4h;Inert atmosphere;	n-BuLi (2 M in hexane, 1.7 mL, 3.45 mmol, 1.5 eqv.) was added to a stirred suspension of methyltriphenylphosphonium bromide (1.23 g, 3.45 mmol, 1.5 eqv.) in dry THF (10 mL) under argon at 0 C dropwise over 5 min, and the resulting solution was allowed to stir for 20 min at 0 C. A solution of the aldehyde 4 (560 mg, 2.30 mmol) in THF (5 mL) was then added dropwise over 5 min with stirring at the same temperature. After 20 min, the solution was allowed to come to room temperature and stirred for another 4 h. The reaction mixture was quenched by addition of aq NH4Cl solution (3 mL) and then extracted with ethyl acetate (2 x 50 mL). The combined organic extract was washed successively with H2O (40 mL) and brine solution (40 mL) and then dried over MgSO4. It was then filtered, and the filtrate was concentrated under reduced pressure to leave the crude product which was purified by column chromatography over silica gel (EtOAc-PE, 1:19) to give the olefin 1b as a colourless liquid (410 mg, 74 %).

References: [1]Journal of Organic Chemistry,2005,vol. 70,p. 5508 - 5518.
[2]Synthetic Communications,2014,vol. 44,p. 2112 - 2120.

17
[ 1826-67-1 ]
[ 147959-19-1 ]
[ 867193-17-7 ]

References: [1]Synlett,2005,p. 2083 - 2085.

18
[ 1099-45-2 ]
[ 147959-19-1 ]
[ 905718-71-0 ]

Yield	Reaction Conditions	Operation in experiment
3.5 g	In tetrahydrofuran; for 12h;Reflux;	To a solution of (ethoxycarbonylmethylene) triphenylphosphorane (6.45 g, 18.51 mmol) in dry THF (30 mL) was added a solution of the above crude aldehyde (3.0 g, 12.34 mmol) in dry THF (25 mL). The reaction mixture was refluxed for 12 h. It was then concentrated and purified by silica gel column chromatography using petroleum ether/EtOAc (8.5:1.5) as eluent to afford the alpha,beta-unsaturated olefin 10 (3.5 g, 80%, after two steps) as a pale yellow liquid; (c 1.2, CHCl3). IR (neat): numax 3384, 2931, 1696, 1595, 1298, 982 cm-1. 1H NMR (200 MHz, CDCl3): delta 1.22 (t, J = 7.20 Hz, 3H), 1.40 (s, 9H), 1.48 (s, 3H), 1.54 (s, 3H), 2.35-2.66 (m, 2H), 3.59-3.68 (m, 1H), 3.83-3.90 (m, 2H), 4.12 (q, J = 7.15 Hz, 2H), 5.79 (d, J = 15.60 Hz, 1H), 6.82 (m, 1H). 13C NMR (50 MHz, CDCl3): delta 14.2, 26.7, 27.3, 28.4, 35.6, 56.1, 60.2, 66.8, 80.3, 94.0, 123.7, 128.9, 144.6, 166.2. ESI[MS](m/z): 336.12 [M++Na]. Anal. Calcd for C16H27NO5: C, 61.32; H, 8.68; N, 4.47%. Found: C, 61.48; H, 8.55; N, 4.51%.

References: [1]Synlett,2006,p. 1181 - 1184.
[2]Tetrahedron Asymmetry,2011,vol. 22,p. 1234 - 1238.

19
[ 130622-08-1 ]
[ 147959-19-1 ]

References: [1]Synlett,2006,p. 1181 - 1184.
[2]Chemistry - An Asian Journal,2015,vol. 10,p. 474 - 482.

20
[ 128427-10-1 ]
[ 147959-19-1 ]

References: [1]Synlett,2006,p. 1181 - 1184.
[2]Organic Letters,2005,vol. 7,p. 1423 - 1426.
[3]Journal of Medicinal Chemistry,1997,vol. 40,p. 495 - 505.
[4]Tetrahedron Asymmetry,2011,vol. 22,p. 1855 - 1860.
[5]Chemistry - An Asian Journal,2015,vol. 10,p. 474 - 482.
[6]Patent: WO2015/164308,2015,A1 .

21
[ 147959-19-1 ]
5-tert-butoxycarbonylamino-6-hydroxy-hex-2-enoic acid ethyl ester [ No CAS ]

References: [1]Synlett,2006,p. 1181 - 1184.
[2]Tetrahedron Asymmetry,2011,vol. 22,p. 1234 - 1238.

22
[ 147959-19-1 ]
[ 905718-72-1 ]

References: [1]Synlett,2006,p. 1181 - 1184.

23
[ 147959-19-1 ]
[ 251325-69-6 ]

References: [1]Synlett,2005,p. 2083 - 2085.

24
[ 147959-19-1 ]
[ 867193-19-9 ]

References: [1]Synlett,2005,p. 2083 - 2085.

25
[ 147959-19-1 ]
[ 867193-18-8 ]

References: [1]Synlett,2005,p. 2083 - 2085.

26
[ 147959-19-1 ]
[ 145206-40-2 ]