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Chemical Structure| 1207163-87-8
Chemical Structure| 1207163-87-8
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Product Details of [ 1207163-87-8 ]

CAS No. :1207163-87-8 MDL No. :MFCD15071777
Formula : C17H21NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :ROTZQDUXIIVXAA-UHFFFAOYSA-N
M.W : 303.35 Pubchem ID :139524288
Synonyms :

Safety of [ 1207163-87-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1207163-87-8 ]

* 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 [ 1207163-87-8 ]

[ 1207163-87-8 ] Synthesis Path-Downstream   1~51

  • 1
  • [ 865758-53-8 ]
  • [ 111-92-2 ]
  • [ 1207163-87-8 ]
  • [ 865758-59-4 ]
YieldReaction ConditionsOperation in experiment
1: 28% 2: 42% With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃; for 1h; microwave irradiation;
  • 2
  • [ 865758-54-9 ]
  • [ 1207163-87-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 - -20 °C 1.2: 80 percent / tetrahydrofuran; hexane / -78 °C 2.1: 98 percent / pyridine; pyridine tribromide; aq. TBAB / CH2Cl2 / 24 h / 20 °C 3.1: 75 percent / t-BuOK / tetrahydrofuran / 0.08 h / 70 °C / microwave irradiation 4.1: 42 percent / BINAP; t-BuONa / Pd2(dba)3 / toluene / 1 h / 100 °C / microwave irradiation
  • 3
  • [ 865758-56-1 ]
  • [ 1207163-87-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 75 percent / t-BuOK / tetrahydrofuran / 0.08 h / 70 °C / microwave irradiation 2: 42 percent / BINAP; t-BuONa / Pd2(dba)3 / toluene / 1 h / 100 °C / microwave irradiation
  • 4
  • [ 865758-55-0 ]
  • [ 1207163-87-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 98 percent / pyridine; pyridine tribromide; aq. TBAB / CH2Cl2 / 24 h / 20 °C 2: 75 percent / t-BuOK / tetrahydrofuran / 0.08 h / 70 °C / microwave irradiation 3: 42 percent / BINAP; t-BuONa / Pd2(dba)3 / toluene / 1 h / 100 °C / microwave irradiation
  • 5
  • [ 93777-26-5 ]
  • [ 1207163-87-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: 90 percent / I2 / CHCl3 / 18 h / 20 °C 2.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 - -20 °C 2.2: 80 percent / tetrahydrofuran; hexane / -78 °C 3.1: 98 percent / pyridine; pyridine tribromide; aq. TBAB / CH2Cl2 / 24 h / 20 °C 4.1: 75 percent / t-BuOK / tetrahydrofuran / 0.08 h / 70 °C / microwave irradiation 5.1: 42 percent / BINAP; t-BuONa / Pd2(dba)3 / toluene / 1 h / 100 °C / microwave irradiation
  • 6
  • [ 1207163-87-8 ]
  • [ 1047657-69-1 ]
YieldReaction ConditionsOperation in experiment
98.7% With hydrogenchloride In ethyl acetate at 15℃; 22 Intermediate: Preparation of (R)-(3H-spiro[benzofuran-2,4'-piperidin]-3-yl)carbamic acid tert-butyl ester I-22g HCl in ethyl acetate (659.30mmol, 4.0M, 165mL, 4.0eq) was added to the reaction flask, and commercially available I-22g-1 (50.00g, 164.83mmol, 1.0eq) in ethyl acetate was added dropwise at 15°C The ester (50 mL) solution was added dropwise, and the reaction was stirred overnight for 15 h. Complete reaction of starting materials was monitored by TLC plate. The reaction solution was directly concentrated to dryness under reduced pressure to obtain white solid I-22g-2 (39.00g, yield 98.7%)
98.7% With hydrogenchloride In ethyl acetate at 15℃; 22 Intermediate: Preparation of (R)-(3H-spiro[benzofuran-2,4'-piperidin]-3-yl)carbamic acid tert-butyl ester I-22g HCl in ethyl acetate (659.30mmol, 4.0M, 165mL, 4.0eq) was added to the reaction flask, and commercially available I-22g-1 (50.00g, 164.83mmol, 1.0eq) in ethyl acetate was added dropwise at 15°C The ester (50 mL) solution was added dropwise, and the reaction was stirred overnight for 15 h. Complete reaction of starting materials was monitored by TLC plate. The reaction solution was directly concentrated to dryness under reduced pressure to obtain white solid I-22g-2 (39.00g, yield 98.7%)
94% With hydrogenchloride; lithium hydroxide monohydrate In 1,4-dioxane at 20℃;
  • 7
  • [ 1207163-55-0 ]
  • [ 1207163-87-8 ]
YieldReaction ConditionsOperation in experiment
75% With potassium <i>tert</i>-butylate In 1,4-dioxane at 70℃; for 2h; d 3H-spiro[l-benzofuran-2.,4,-piperidinl-3-one, Intermediate AP Step d: To a solution of /ert-butyl 4-(2-fluorobenzoyl)-4-hydroxypiperidine-l-carboxylate (600 mg, 1.85 mmol) in dioxane (5 mL) was added /-BuOK (207 mg, 1.85 mmol). The mixture was stirred at 70 °C for 2 hours. The mixture was concentrated under reduced pressure and diluted with water (20 mL), extracted by EtOAc (30 mL x 3). The combined organic layers were washed with brine (30.0 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (petroleum ether : ethyl acetate = 100 : 0 to 100 : 10) to give /cvV-butyl 3- oxo-3i-spiro[l-benzofuran-2,4 (210 mg, 75% yield) as a white solid. LCMS m/z [M-100]+ = 203.9.
70% With potassium <i>tert</i>-butylate In tetrahydrofuran at 70℃; for 2h; Inert atmosphere; 45.4 Step 4 Synthesis of 3-oxo-3H-spiro[benzofuran-2,4'-piperidine]-1'-carboxylic acid tert-butyl ester Dissolve tert-butyl 4-(2-fluorobenzoyl)-4-hydroxypiperidine-1-carboxylate (20.4g, 63.08mmol) inanhydrous tetrahydrofuran (200ml) in a 500ml single-neck flask, and add tert-butyl 4-(2-fluorobenzoyl)-4-hydroxypiperidine-1-carboxylate (20.4g, 63.08mmol) in anhydrous tetrahydrofuran (200ml). Potassium butoxide (10.6g, 94.7mmol), heated to 70°C under nitrogen protection, and reacted for 2h.After thecompletion of the reaction, the reaction solution was poured into 800ml of water, stirred at room temperaturefor 10min, extracted with ethyl acetate (500mL) three times, the organic phase was washed once withsaturated brine, dried with anhydrous sodium sulfate, concentrated, and separated by column chromatographyto obtain a white solid 10.7 g, the yield is 70%.
63% With potassium <i>tert</i>-butylate In 1,4-dioxane Reflux;
8.20 kg With potassium <i>tert</i>-butylate In 2-methyltetrahydrofuran at 25 - 40℃; Large scale; 1.4 Step 4. Preparation of Compound 7 Compound 6 (21.9 kg) was dissolved in 80.0 L of 2-MeTHF, and the mixture was charged into a 200 L enamel reactor and stirred by strong magnetic stirrer. 8.80 kg of t-BuOK was added portion-wise at 25-40° C. The reaction mixture was stirred for 1 hr at 40° C. TLC analysis (petroleum ether/ethyl acetate=3/1) indicated compound 6 was consumed and one new spot (Rf=0.6) was observed. The reaction mixture was cooled to 25° C. 80.0 L of H2O was added slowly to the mixture at 20-25° C. and stirred for 0.5 hr. The organic layer was separated and dried with Na2SO4 (10.0 kg), filtered and the filtrate was concentrated under reduced pressure at 45° C. MTBE (30.0 L) was added when 90% of 2-MeTHF was removed. The mixture was stirred for 1 hr at 20° C. The mixture was filtered, and the white solid was obtained. The white solid was dried under reduced pressure at 45° C. Compound 7 (8.20 kg) was obtained as white solid, which was confirmed by 1H NMR. 1H NMR: (400 MHz CDCl3) δ 7.64-7.54 (m, 2H), 7.09-6.99 (m, 2H), 4.08 (br s, 2H), 3.34-3.01 (m, 2H), 1.92-1.84 (m, 2H), 1.51 (br d, J=16.0 Hz, 2H), 1.42 (s, 9H).

  • 8
  • [ 446-52-6 ]
  • [ 1207163-87-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: boron trifluoride diethyl etherate / dichloromethane / 0 - 25 °C 2.1: lithium diisopropyl amide / tetrahydrofuran / -78 - -20 °C 2.2: 2 h / -78 °C 3.1: water; pyridine; pyridinium hydrobromide perbromide; tetrabutylammomium bromide / dichloromethane / 12 h / 25 °C 4.1: potassium <i>tert</i>-butylate / 1,4-dioxane / 2 h / 70 °C
Multi-step reaction with 4 steps 1.1: iodine / dichloromethane / 18 h / 20 °C / Inert atmosphere 2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere 2.2: -78 °C 3.1: pyridine; tetrabutylammomium bromide; pyridinium hydrobromide perbromide / water / 24 h / 20 °C 4.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / 70 °C / Inert atmosphere
Multi-step reaction with 4 steps 1.1: iodine / dichloromethane / 8 h / 20 - 35 °C / Large scale 1.2: 0.5 h / 25 - 30 °C / Large scale 2.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -5 - 5 °C / Inert atmosphere; Large scale 2.2: 1 h / -5 - 5 °C / Inert atmosphere; Large scale 3.1: tetrabutylammomium bromide; pyridine; pyridinium hydrobromide perbromide; water / dichloromethane / 0.5 h / 10 - 20 °C / Large scale 4.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 25 - 40 °C / Large scale
  • 9
  • [ 138036-92-7 ]
  • [ 1207163-87-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / -78 - -20 °C 1.2: 2 h / -78 °C 2.1: water; pyridine; pyridinium hydrobromide perbromide; tetrabutylammomium bromide / dichloromethane / 12 h / 25 °C 3.1: potassium <i>tert</i>-butylate / 1,4-dioxane / 2 h / 70 °C
Multi-step reaction with 3 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere 1.2: -78 °C 2.1: pyridine; tetrabutylammomium bromide; pyridinium hydrobromide perbromide / water / 24 h / 20 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / 70 °C / Inert atmosphere
Multi-step reaction with 3 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -5 - 5 °C / Inert atmosphere; Large scale 1.2: 1 h / -5 - 5 °C / Inert atmosphere; Large scale 2.1: tetrabutylammomium bromide; pyridine; pyridinium hydrobromide perbromide; water / dichloromethane / 0.5 h / 10 - 20 °C / Large scale 3.1: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 25 - 40 °C / Large scale
  • 10
  • [ 2377355-30-9 ]
  • [ 1207163-87-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: water; pyridine; pyridinium hydrobromide perbromide; tetrabutylammomium bromide / dichloromethane / 12 h / 25 °C 2: potassium <i>tert</i>-butylate / 1,4-dioxane / 2 h / 70 °C
Multi-step reaction with 2 steps 1: pyridine; tetrabutylammomium bromide; pyridinium hydrobromide perbromide / water / 24 h / 20 °C 2: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / 70 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: tetrabutylammomium bromide; pyridine; pyridinium hydrobromide perbromide; water / dichloromethane / 0.5 h / 10 - 20 °C / Large scale 2: potassium <i>tert</i>-butylate / 2-methyltetrahydrofuran / 25 - 40 °C / Large scale
  • 11
  • [ 1207163-87-8 ]
  • [ 2377359-42-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 12 h / 80 °C / Inert atmosphere 2: lithium borohydride / tetrahydrofuran / 2 h / 0 - 25 °C 3: hydrogenchloride / methanol / 0.5 h / 60 °C 4: triethylamine / N,N-dimethyl-formamide / 12 h / 70 °C 5: N,N-dimethyl-formamide / 2 h / 70 °C 6: triethylsilane; 9-[5-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl]diphenyl-λ4-phosphanyl}-O-methanesulfonyl-8-methyl-8λ4-aza-9-palladatricyclo[8.4.0.02,7]tetradeca-1(14),2,4,6,10,12-hexaene-9,9-bis(ylium)-10-uid-9-olate; caesium carbonate / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere
  • 12
  • [ 1207163-87-8 ]
  • [ 2377353-05-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 12 h / 80 °C / Inert atmosphere 2: lithium borohydride / tetrahydrofuran / 2 h / 0 - 25 °C 3: hydrogenchloride / methanol / 0.5 h / 60 °C 4: triethylamine / N,N-dimethyl-formamide / 12 h / 70 °C 5: N,N-dimethyl-formamide / 2 h / 70 °C 6: triethylsilane; 9-[5-(diphenylphosphanyl)-9,9-dimethyl-9H-xanthen-4-yl]diphenyl-λ4-phosphanyl}-O-methanesulfonyl-8-methyl-8λ4-aza-9-palladatricyclo[8.4.0.02,7]tetradeca-1(14),2,4,6,10,12-hexaene-9,9-bis(ylium)-10-uid-9-olate; caesium carbonate / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere 7: water; hydrogenchloride / tetrahydrofuran / 12 h / 30 °C
  • 13
  • [ 1207163-87-8 ]
  • [ 2377359-45-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 12 h / 80 °C / Inert atmosphere 2: lithium borohydride / tetrahydrofuran / 2 h / 0 - 25 °C 3: hydrogenchloride / methanol / 0.5 h / 60 °C 4: triethylamine / dimethyl sulfoxide / 4 h / 80 °C 5: dimethyl sulfoxide / 0.5 h / 20 °C
  • 14
  • [ 1207163-87-8 ]
  • [ 2632929-04-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 12 h / 80 °C / Inert atmosphere 2: lithium borohydride / tetrahydrofuran / 2 h / 0 - 25 °C 3: hydrogenchloride / methanol / 0.5 h / 60 °C 4: triethylamine / dimethyl sulfoxide / 4 h / 80 °C
Multi-step reaction with 3 steps 1.1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 40 h / 75 - 80 °C / Inert atmosphere; Large scale 1.2: 0.5 h / 0 - 10 °C / Inert atmosphere; Large scale 2.1: hydrogenchloride / methanol / 4 h / 20 - 25 °C / Large scale 3.1: potassium carbonate / dimethyl sulfoxide / 60 - 65 °C / Inert atmosphere
  • 15
  • [ 1207163-87-8 ]
  • [ 2377359-46-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 12 h / 80 °C / Inert atmosphere 2: lithium borohydride / tetrahydrofuran / 2 h / 0 - 25 °C 3: hydrogenchloride / methanol / 0.5 h / 60 °C 4: triethylamine / dimethyl sulfoxide / 4 h / 80 °C 5: dimethyl sulfoxide / 0.5 h / 20 °C 6: N-Bromosuccinimide; acetic acid / acetonitrile / 1 h / 20 °C
  • 16
  • [ 1207163-87-8 ]
  • [ 2377359-75-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 12 h / 80 °C / Inert atmosphere 2: lithium borohydride / tetrahydrofuran / 2 h / 0 - 25 °C 3: hydrogenchloride / methanol / 0.5 h / 60 °C 4: triethylamine / N,N-dimethyl-formamide / 12 h / 85 °C 5: N,N-dimethyl-formamide / 2 h / 70 °C 6: water; potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos / 1,4-dioxane / 3 h / 100 °C / Inert atmosphere
  • 17
  • [ 1207163-87-8 ]
  • [ 2377359-76-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 12 h / 80 °C / Inert atmosphere 2: lithium borohydride / tetrahydrofuran / 2 h / 0 - 25 °C 3: hydrogenchloride / methanol / 0.5 h / 60 °C 4: triethylamine / N,N-dimethyl-formamide / 12 h / 85 °C 5: N,N-dimethyl-formamide / 2 h / 70 °C 6: water; potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos / 1,4-dioxane / 3 h / 100 °C / Inert atmosphere 7: caesium carbonate / N,N-dimethyl-formamide / 2.5 h / 80 °C
  • 18
  • [ 1207163-87-8 ]
  • [ 2377359-77-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 12 h / 80 °C / Inert atmosphere 2: lithium borohydride / tetrahydrofuran / 2 h / 0 - 25 °C 3: hydrogenchloride / methanol / 0.5 h / 60 °C 4: triethylamine / N,N-dimethyl-formamide / 12 h / 85 °C 5: N,N-dimethyl-formamide / 2 h / 70 °C 6: water; potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos / 1,4-dioxane / 3 h / 100 °C / Inert atmosphere 7: caesium carbonate / N,N-dimethyl-formamide / 2.5 h / 80 °C 8: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate / toluene / 12 h / 100 °C / Inert atmosphere
  • 19
  • [ 1207163-87-8 ]
  • [ 2377353-42-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 12 h / 80 °C / Inert atmosphere 2: lithium borohydride / tetrahydrofuran / 2 h / 0 - 25 °C 3: hydrogenchloride / methanol / 0.5 h / 60 °C 4: triethylamine / N,N-dimethyl-formamide / 12 h / 85 °C 5: N,N-dimethyl-formamide / 2 h / 70 °C 6: water; potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos / 1,4-dioxane / 3 h / 100 °C / Inert atmosphere 7: caesium carbonate / N,N-dimethyl-formamide / 2.5 h / 80 °C 8: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate / toluene / 12 h / 100 °C / Inert atmosphere 9: hydrogenchloride / methanol / 3 h / 25 °C
  • 20
  • [ 1207163-87-8 ]
  • [ 2377360-31-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 12 h / 80 °C / Inert atmosphere 2: lithium borohydride / tetrahydrofuran / 2 h / 0 - 25 °C 3: hydrogenchloride / methanol / 0.5 h / 60 °C 4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 100 °C
  • 21
  • [ 1207163-87-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 12 h / 80 °C / Inert atmosphere 2: lithium borohydride / tetrahydrofuran / 2 h / 0 - 25 °C 3: hydrogenchloride / methanol / 0.5 h / 60 °C 4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 100 °C 5: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C / Inert atmosphere
  • 22
  • [ 1207163-87-8 ]
  • [ 1047721-77-6 ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: 3-oxo-3H-spiro[benzofuran-2,4'-piperidine]-1'-carboxylic acid tert-butyl ester With hydrogenchloride In 1,4-dioxane at 20℃; for 12h; Stage #2: With methanol; potassium carbonate e 3H-spiro[l-benzofuran-2.,4,-piperidinl-3-one, Intermediate AP Step e: To a solution of /ert-butyl 3-oxo-3//-spiro[ l -benzofuran-2,4'-piperidine]- 1 carboxylate (300 mg, 988 pmol) in dioxane (2 mL) was added HCl/dioxane (2.46 mL, 4M). The mixture was stirred at 20 °C for 12 hours. The reaction mixture was concentrated to dryness, MeOH (2 mL) and K2C03 (100 mg) were added. The mixture was filtered and the filtrate was concentrated to dryness to give 3//-spiro[ l -benzofuran-2,4'-piperidin]-3-one (150 mg, 75% yield) as a white solid. LCMS m/z [M+H]+ = 204.9.
  • 23
  • [ 1207163-87-8 ]
  • [ 2377356-08-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 12 h / 80 °C / Inert atmosphere 2: lithium borohydride / tetrahydrofuran / 2 h / 0 - 25 °C
Multi-step reaction with 2 steps 1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 90 °C / Inert atmosphere 2: lithium borohydride / tetrahydrofuran / 1 h / 0 °C
  • 24
  • [ 1207163-87-8 ]
  • [ 2377356-06-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 12 h / 80 °C / Inert atmosphere 2: lithium borohydride / tetrahydrofuran / 2 h / 0 - 25 °C 3: hydrogenchloride / methanol / 0.5 h / 60 °C
Multi-step reaction with 2 steps 1.1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 40 h / 75 - 80 °C / Inert atmosphere; Large scale 1.2: 0.5 h / 0 - 10 °C / Inert atmosphere; Large scale 2.1: hydrogenchloride / methanol / 4 h / 20 - 25 °C / Large scale
  • 25
  • [ 1207163-87-8 ]
  • [ 2377356-22-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 12 h / 80 °C / Inert atmosphere 2: lithium borohydride / tetrahydrofuran / 2 h / 0 - 25 °C 3: hydrogenchloride / methanol / 0.5 h / 60 °C 4: triethylamine / N,N-dimethyl-formamide / 12 h / 85 °C
  • 26
  • [ 1207163-87-8 ]
  • [ 2377356-21-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 12 h / 80 °C / Inert atmosphere 2: lithium borohydride / tetrahydrofuran / 2 h / 0 - 25 °C 3: hydrogenchloride / methanol / 0.5 h / 60 °C 4: triethylamine / N,N-dimethyl-formamide / 12 h / 85 °C 5: N,N-dimethyl-formamide / 2 h / 70 °C
  • 27
  • [ 1207163-87-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 12 h / 80 °C / Inert atmosphere 2: lithium borohydride / tetrahydrofuran / 2 h / 0 - 25 °C 3: hydrogenchloride / methanol / 0.5 h / 60 °C 4: triethylamine / N,N-dimethyl-formamide / 12 h / 70 °C
  • 28
  • [ 1207163-87-8 ]
  • [ 2377356-55-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 12 h / 80 °C / Inert atmosphere 2: lithium borohydride / tetrahydrofuran / 2 h / 0 - 25 °C 3: hydrogenchloride / methanol / 0.5 h / 60 °C 4: triethylamine / N,N-dimethyl-formamide / 12 h / 70 °C 5: N,N-dimethyl-formamide / 2 h / 70 °C
  • 29
  • [ 1207163-87-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 12 h / 80 °C / Inert atmosphere 2: lithium borohydride / tetrahydrofuran / 2 h / 0 - 25 °C 3: hydrogenchloride / methanol / 0.5 h / 60 °C 4: sodium carbonate / 1-methyl-pyrrolidin-2-one / 1 h / 130 °C
  • 30
  • [ 1207163-87-8 ]
  • [ 2377357-04-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 12 h / 80 °C / Inert atmosphere 2: lithium borohydride / tetrahydrofuran / 2 h / 0 - 25 °C 3: hydrogenchloride / methanol / 0.5 h / 60 °C 4: sodium carbonate / 1-methyl-pyrrolidin-2-one / 1 h / 130 °C 5: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 12 h / 25 °C
  • 31
  • [ 1207163-87-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 12 h / 80 °C / Inert atmosphere 2: lithium borohydride / tetrahydrofuran / 2 h / 0 - 25 °C 3: hydrogenchloride / methanol / 0.5 h / 60 °C 4: sodium carbonate / 1-methyl-pyrrolidin-2-one / 1 h / 130 °C 5: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 12 h / 25 °C 6: sodium ethanolate; ethanol / tetrahydrofuran / 2 h / 0 - 25 °C
  • 32
  • [ 1207163-87-8 ]
  • [ 2377357-31-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 12 h / 80 °C / Inert atmosphere 2: lithium borohydride / tetrahydrofuran / 2 h / 0 - 25 °C 3: trifluoroacetic acid / dichloromethane / 2 h / 30 °C
Multi-step reaction with 3 steps 1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 90 °C / Inert atmosphere 2: lithium borohydride / tetrahydrofuran / 1 h / 0 °C 3: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
  • 33
  • [ 1207163-87-8 ]
  • [ 2377358-10-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: hydrogenchloride / 1,4-dioxane / 12 h / 20 °C 2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 11.5 h / 10 °C / Inert atmosphere
  • 34
  • [ 1207163-87-8 ]
  • [ 2377358-11-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hydrogenchloride / 1,4-dioxane / 12 h / 20 °C 2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 11.5 h / 10 °C / Inert atmosphere 3.1: water; pyridine; pyridinium hydrobromide perbromide; tetrabutylammomium bromide / dichloromethane / 12 h / 25 °C
  • 35
  • [ 1207163-87-8 ]
  • [ 2377358-12-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: hydrogenchloride / 1,4-dioxane / 12 h / 20 °C 2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 11.5 h / 10 °C / Inert atmosphere 3.1: water; pyridine; pyridinium hydrobromide perbromide; tetrabutylammomium bromide / dichloromethane / 12 h / 25 °C 4.1: potassium <i>tert</i>-butylate / 1,4-dioxane / 2 h / 70 °C
  • 36
  • [ 1207163-87-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: hydrogenchloride / 1,4-dioxane / 12 h / 20 °C 2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 11.5 h / 10 °C / Inert atmosphere 3.1: water; pyridine; pyridinium hydrobromide perbromide; tetrabutylammomium bromide / dichloromethane / 12 h / 25 °C 4.1: potassium <i>tert</i>-butylate / 1,4-dioxane / 2 h / 70 °C 5.1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 12 h / 90 °C / Inert atmosphere
  • 37
  • [ 1207163-87-8 ]
  • [ 2377358-09-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: hydrogenchloride / 1,4-dioxane / 12 h / 20 °C 2.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 11.5 h / 10 °C / Inert atmosphere 3.1: water; pyridine; pyridinium hydrobromide perbromide; tetrabutylammomium bromide / dichloromethane / 12 h / 25 °C 4.1: potassium <i>tert</i>-butylate / 1,4-dioxane / 2 h / 70 °C 5.1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 12 h / 90 °C / Inert atmosphere 6.1: lithium borohydride / 2-methyltetrahydrofuran / 2 h / -78 °C
  • 38
  • [ 1207163-87-8 ]
  • [ 2377358-66-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogenchloride / 1,4-dioxane / 12 h / 20 °C 2: triethylamine / N,N-dimethyl-formamide / 12 h / 80 °C
  • 39
  • [ 1207163-87-8 ]
  • [ 2377358-67-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogenchloride / 1,4-dioxane / 12 h / 20 °C 2: triethylamine / N,N-dimethyl-formamide / 12 h / 80 °C 3: ethanol; ammonium acetate; sodium cyanoborohydride / 12 h / 60 °C
  • 40
  • [ 1207163-87-8 ]
  • [ 2377358-69-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogenchloride / 1,4-dioxane / 12 h / 20 °C 2: triethylamine / N,N-dimethyl-formamide / 12 h / 80 °C 3: ethanol; ammonium acetate; sodium cyanoborohydride / 12 h / 60 °C 4: hydrogenchloride; methanol / 2 h / 20 °C
  • 41
  • [ 1207163-87-8 ]
  • [ 2377352-49-1 ]
  • [ 2377352-48-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogenchloride / 1,4-dioxane / 12 h / 20 °C 2: triethylamine / N,N-dimethyl-formamide / 12 h / 80 °C 3: ethanol; ammonium acetate; sodium cyanoborohydride / 12 h / 60 °C 4: hydrogenchloride; methanol / 2 h / 20 °C 5: ammonium hydroxide / ethanol / Resolution of racemate
  • 42
  • [ 1207163-87-8 ]
  • [ 196929-78-9 ]
  • [ 2377356-07-3 ]
YieldReaction ConditionsOperation in experiment
97% With titanium(IV) tetraethanolate In 2-methyltetrahydrofuran at 90℃; Inert atmosphere; 45.5 Step 5 Synthesis of (R,Z)-3-((tert-butylsulfinyl)imino)-3H-spiro[benzofuran-2,4'-piperidine]-1'-carboxylic acid tert-butyl ester In a 500mL single-neck flask, dissolve 3-oxo-3H-spiro[benzofuran-2,4'-piperidine]-1'-carboxylic acidtert-butyl ester (10.7g, 35.27mmol) in anhydrous 2- To methyltetrahydrofuran (100mL), R-tert-butylsulfinamide (12.82g, 105.8mmol) and tetraethoxytitanium (37mL, 176.35mmol) were added, and thetemperature was raised to 90°C for overnight reaction under the protection of nitrogen.After the reaction iscomplete, pour the reaction solution into water (800ml) and at the same time add ethyl acetate (800ml), stir atroom temperature for 15 minutes and then filter through Celite. Wash the filtrate once with a saturated aqueoussodium chloride solution, dry and concentrate, and perform the column layer Analytical separation yielded9.17 g of the title product with a yield of 97%.
With titanium(IV) tetraethanolate In 2-methyltetrahydrofuran at 80℃; for 12h; Inert atmosphere; a (R)-3H-spirofbenzofuran-2,4'-piperidinl-5-amine, Intermediate CB Step a: A mixture oftert-butyl 3-oxo-3H-spiro[benzofuran-2,4'-piperidine]-l'- carboxylate (200 mg, 659 pmol, synthesized via Steps a-d of Intermediate AP), Ti(OEt)4 (599 mg, 2.63 mmol) and(R)-2-methylpropane-2-sulfmamide (119 mg, 988 umol) in 2-Me-THF (10 mL) was stirred at 80 °C for 12 hours under N2 atmosphere. The reaction mixture was then concentrated to give tert-butyl (R,Z)-3-((tert-butylsulfmyl)imino)-3H-spiro[benzofuran-2,4'-piperidine]-l'-carboxylate (600 mg, quant crude yield). LCMS m/z [M+Na]+ = 429.0.
  • 43
  • [ 1207163-87-8 ]
  • [ 2377352-49-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 40 h / 75 - 80 °C / Inert atmosphere; Large scale 1.2: 0.5 h / 0 - 10 °C / Inert atmosphere; Large scale 2.1: hydrogenchloride / methanol / 4 h / 20 - 25 °C / Large scale 3.1: potassium carbonate / dimethyl sulfoxide / 60 - 65 °C / Inert atmosphere 4.1: hydrogenchloride / methanol / 0 - 30 °C / Inert atmosphere 5.1: sodium hydroxide / water; methanol / 0 - 5 °C / Inert atmosphere
  • 44
  • [ 1207163-87-8 ]
  • [ 2632928-85-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 40 h / 75 - 80 °C / Inert atmosphere; Large scale 1.2: 0.5 h / 0 - 10 °C / Inert atmosphere; Large scale 2.1: hydrogenchloride / methanol / 4 h / 20 - 25 °C / Large scale 3.1: potassium carbonate / dimethyl sulfoxide / 60 - 65 °C / Inert atmosphere 4.1: hydrogenchloride / methanol / 0 - 30 °C / Inert atmosphere
  • 45
  • [ 1207163-87-8 ]
  • [ 2632928-84-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 40 h / 75 - 80 °C / Inert atmosphere; Large scale 1.2: 0.5 h / 0 - 10 °C / Inert atmosphere; Large scale 2.1: hydrogenchloride / methanol / 4 h / 20 - 25 °C / Large scale 3.1: potassium carbonate / dimethyl sulfoxide / 60 - 65 °C / Inert atmosphere 4.1: hydrogenchloride / methanol / 0 - 30 °C / Inert atmosphere 5.1: sodium hydroxide / water; methanol / 0 - 5 °C / Inert atmosphere 6.1: hydrogen bromide / acetonitrile / 64 h / 5 - 50 °C
  • 46
  • [ 1207163-87-8 ]
  • [ 2632928-86-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 40 h / 75 - 80 °C / Inert atmosphere; Large scale 1.2: 0.5 h / 0 - 10 °C / Inert atmosphere; Large scale 2.1: hydrogenchloride / methanol / 4 h / 20 - 25 °C / Large scale 3.1: potassium carbonate / dimethyl sulfoxide / 60 - 65 °C / Inert atmosphere 4.1: hydrogenchloride / methanol / 0 - 30 °C / Inert atmosphere 5.1: sodium hydroxide / water; methanol / 0 - 5 °C / Inert atmosphere 6.1: sulfuric acid / acetonitrile / 64 h / 5 - 50 °C
  • 47
  • [ 1207163-87-8 ]
  • [ 2632928-87-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: titanium(IV) tetraethanolate / 2-methyltetrahydrofuran / 40 h / 75 - 80 °C / Inert atmosphere; Large scale 1.2: 0.5 h / 0 - 10 °C / Inert atmosphere; Large scale 2.1: hydrogenchloride / methanol / 4 h / 20 - 25 °C / Large scale 3.1: potassium carbonate / dimethyl sulfoxide / 60 - 65 °C / Inert atmosphere 4.1: hydrogenchloride / methanol / 0 - 30 °C / Inert atmosphere 5.1: sodium hydroxide / water; methanol / 0 - 5 °C / Inert atmosphere 6.1: acetonitrile / 64 h / 5 - 50 °C
  • 48
  • [ 1207163-87-8 ]
  • [ 196929-78-9 ]
  • [ 2377356-08-4 ]
YieldReaction ConditionsOperation in experiment
50% Stage #1: 3-oxo-3H-spiro[benzofuran-2,4'-piperidine]-1'-carboxylic acid tert-butyl ester; (R)-2-methylpropane-2-sulfinamide With titanium(IV) tetraethanolate In 2-methyltetrahydrofuran at 75 - 80℃; for 40h; Inert atmosphere; Large scale; Stage #2: With lithium borohydride In 2-methyltetrahydrofuran at 0 - 10℃; for 0.5h; Inert atmosphere; Large scale; 1.5 Step 5. Preparation of Compound 8 (The reaction disclosed in Step 5 was performed in 2 parallel batches.) 16.0 L of 2-MeTHF was charged into a 50 L reaction still and stirred by strong magnetic stirrer. 4.10 kg of compound 7, 3.28 kg of compound 7-1 and 10.2 kg of Ti(OEt)4 were added in one portion. The reaction mixture was heated to 75° C. and stirred for 40 hrs at 75-80° C. under N2. TLC analysis (petroleum ether/ethyl acetate=3/1) indicated a small amount of compound 7 (Rf=0.7) was retained and one new spot (Rf=0.5) was observed. The reaction mixture was cooled to 0° C. 300 g of LiBH4 was added portion-wise at 0-10° C. under N2. The reaction mixture was stirred for 0.5 hr at 0-10° C. under N2. TLC analysis (petroleum ether/ethyl acetate=3/1) indicated the spot (Rf=0.5) was consumed and one new spot (Rf=0.3) was observed. To the reaction mixture was added MeOH (4.00 L) slowly at 25-30° C. About 80.0 L of mixture was obtained. 8.00 kg of EDTE was added to the mixture and stirred for 1 hr. 10.0 L of the mixture was added to citric acid (20.0 L, 10% water solution) and ethyl acetate (10.0 L). The organic layer was separated and washed with NaHCO3 (10.0 L, 10% water solution). Eight batches of organic layers were obtained and dried with Na2SO4 (10.0 kg), filtered and the filtrate was concentrated under reduced pressure at 45° C. To the crude product was added MTBE (20.0 L) and the mixture was stirred for 1 hr. The mixture was filtered, and the cake was obtained. To the filter cake was added DCM (40.0 L) and filtered with silica gel (3.00 kg). The filtrate was concentrated under reduce pressure at 45° C. Then MTBE (15.0 L) was added to the crude product and stirred for 1 hr. The mixture was filtered, and a white solid was obtained. The white solid was dried under reduce pressure at 40° C. Compound 8 (5.40 kg, yield: 50%) was obtained, which was confirmed by HPLC and 1H NMR. 1H NMR: (400 MHz CDCl3) δ 7.26-7.12 (m, 2H), 6.86-6.83 (m, 1H), 6.74 (d, J=8.0 Hz, 1H), 4.56 (br d, J=8.0 Hz, 1H), 4.01 (br s, 2H), 3.61 (br d, J=8.0 Hz, 1H), 3.2-2.90 (m, 2H), 2.03-1.57 (m, 4H), 1.39 (s, 9H), 1.18 (s, 9H).
  • 49
  • [ 1207163-87-8 ]
  • [ 2377357-01-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: hydrogenchloride / ethyl acetate / 15 °C 2: anhydrous sodium carbonate / lithium hydroxide monohydrate; tetrahydrofuran / 15 h / 0 - 20 °C 3: tetraethyl titanate / tetrahydrofuran / 17 h / 70 - 80 °C 4: borane-THF / tetrahydrofuran / 0.5 h / -25 - -20 °C 5: anhydrous sodium carbonate / lithium hydroxide monohydrate; tetrahydrofuran / 15 h / 15 °C 6: hydrogen; palladium hydroxide on carbon / methanol / 15 h / 15 °C
Multi-step reaction with 6 steps 1: hydrogenchloride / ethyl acetate / 15 °C 2: anhydrous sodium carbonate / lithium hydroxide monohydrate; tetrahydrofuran / 15 h / 0 - 20 °C 3: tetraethyl titanate / tetrahydrofuran / 46 h / 70 - 80 °C 4: borane-THF / tetrahydrofuran / 0.5 h / -25 - -20 °C 5: anhydrous sodium carbonate / lithium hydroxide monohydrate; tetrahydrofuran / 15 h / 10 - 15 °C 6: hydrogen; palladium hydroxide on carbon / methanol / 15 h / 15 °C
  • 50
  • [ 1207163-87-8 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: hydrogenchloride / ethyl acetate / 15 °C 2: anhydrous sodium carbonate / lithium hydroxide monohydrate; tetrahydrofuran / 15 h / 0 - 20 °C 3: tetraethyl titanate / tetrahydrofuran / 17 h / 70 - 80 °C 4: borane-THF / tetrahydrofuran / 0.5 h / -25 - -20 °C 5: anhydrous sodium carbonate / lithium hydroxide monohydrate; tetrahydrofuran / 15 h / 15 °C 6: hydrogen; palladium hydroxide on carbon / methanol / 15 h / 15 °C 7: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 1 h / 140 °C / Microwave irradiation
Multi-step reaction with 7 steps 1: hydrogenchloride / ethyl acetate / 15 °C 2: anhydrous sodium carbonate / lithium hydroxide monohydrate; tetrahydrofuran / 15 h / 0 - 20 °C 3: tetraethyl titanate / tetrahydrofuran / 46 h / 70 - 80 °C 4: borane-THF / tetrahydrofuran / 0.5 h / -25 - -20 °C 5: anhydrous sodium carbonate / lithium hydroxide monohydrate; tetrahydrofuran / 15 h / 10 - 15 °C 6: hydrogen; palladium hydroxide on carbon / methanol / 15 h / 15 °C 7: N-ethyl-N,N-diisopropylamine / 1-methyl-pyrrolidin-2-one / 1 h / 140 °C / Microwave irradiation
  • 51
  • [ 1207163-87-8 ]
  • [ 2761178-24-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydrogenchloride / ethyl acetate / 15 °C 2: anhydrous sodium carbonate / lithium hydroxide monohydrate; tetrahydrofuran / 15 h / 0 - 20 °C 3: tetraethyl titanate / tetrahydrofuran / 17 h / 70 - 80 °C 4: borane-THF / tetrahydrofuran / 0.5 h / -25 - -20 °C 5: anhydrous sodium carbonate / lithium hydroxide monohydrate; tetrahydrofuran / 15 h / 15 °C
Multi-step reaction with 5 steps 1: hydrogenchloride / ethyl acetate / 15 °C 2: anhydrous sodium carbonate / lithium hydroxide monohydrate; tetrahydrofuran / 15 h / 0 - 20 °C 3: tetraethyl titanate / tetrahydrofuran / 46 h / 70 - 80 °C 4: borane-THF / tetrahydrofuran / 0.5 h / -25 - -20 °C 5: anhydrous sodium carbonate / lithium hydroxide monohydrate; tetrahydrofuran / 15 h / 10 - 15 °C
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