3-(1-苄基哌啶-2-基)丙-1-醇

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Oxalyl chloride (0.55 mL, 6.44 mmol) was added to a stirred solution of DMSO (0.92 mL, 12.87 mmol) in dry DCM (40 mL) at −78° C. and the reaction mixture was stirred for 15 minutes. Compound 22 (1 g, 4.29 mmol) dissolved in DCM (15 mL) was the added drop-wise and the reaction mixture was stirred at −78° C. for 1 hour. The reaction mixture was then quenched by adding Et3N (2.9 mL, 21.45 mmol) drop-wise and the solution was stirred at rt for 15 minutes. Water was then added to the solution and the reaction mixture was extracted with DCM. The organic layer was dried over Na2SO4, filtered and concentrated to yield crude compound 23 which was used as such for the next step. the reaction mixture was stirred at −78° C. for 1 hour The reaction mixture was then quenched the solution was stirred at rt for 15 minutes the reaction mixture was extracted with DCM The organic layer was dried over Na2SO4 filtered concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a stirred solution of compound 21 (3 g, 16.71 mmol) in ethanol (23 mL) was added K2CO3 (11.5 g, 83.55 mmol) portion-wise at ice cold conditions. Benzyl bromide (2 mL, 16.71 mmol) was then added and the reaction mixture was heated at reflux for 2 hours. The reaction mixture was filtered, and washed with EtOAc. The filtrate was concentrated, the residue was dissolved in EtOAc, washed with saturated NaHCO3 solution and brine, dried over Na2SO4, filtered and concentrated. The crude material was purified by 230-400 silica gel column chromatography using 1-3% MeOH-DCM as eluent to yield compound 22. the reaction mixture was heated at reflux for 2 hours The reaction mixture was filtered washed with EtOAc The filtrate was concentrated the residue was dissolved in EtOAc washed with saturated NaHCO3 solution and brine dried over Na2SO4 filtered concentrated The crude material was purified by 230-400 silica gel column chromatography

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a stirred solution of compound 21 (3 g, 16.71 mmol) in ethanol (23 mL) was added K2CO3 (11.5 g, 83.55 mmol) portion-wise at ice cold conditions. Benzyl bromide (2 mL, 16.71 mmol) was then added and the reaction mixture was heated at reflux for 2 hours. The reaction mixture was filtered, and washed with EtOAc. The filtrate was concentrated, the residue was dissolved in EtOAc, washed with saturated NaHCO3 solution and brine, dried over Na2SO4, filtered and concentrated. The crude material was purified by 230-400 silica gel column chromatography using 1-3% MeOH-DCM as eluent to yield compound 22. the reaction mixture was heated at reflux for 2 hours The reaction mixture was filtered washed with EtOAc The filtrate was concentrated the residue was dissolved in EtOAc washed with saturated NaHCO3 solution and brine dried over Na2SO4 filtered concentrated The crude material was purified by 230-400 silica gel column chromatography

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Oxalyl chloride (0.55 mL, 6.44 mmol) was added to a stirred solution of DMSO (0.92 mL, 12.87 mmol) in dry DCM (40 mL) at −78° C. and the reaction mixture was stirred for 15 minutes. Compound 22 (1 g, 4.29 mmol) dissolved in DCM (15 mL) was the added drop-wise and the reaction mixture was stirred at −78° C. for 1 hour. The reaction mixture was then quenched by adding Et3N (2.9 mL, 21.45 mmol) drop-wise and the solution was stirred at rt for 15 minutes. Water was then added to the solution and the reaction mixture was extracted with DCM. The organic layer was dried over Na2SO4, filtered and concentrated to yield crude compound 23 which was used as such for the next step. the reaction mixture was stirred at −78° C. for 1 hour The reaction mixture was then quenched the solution was stirred at rt for 15 minutes the reaction mixture was extracted with DCM The organic layer was dried over Na2SO4 filtered concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Oxalyl chloride (0.55 mL, 6.44 mmol) was added to a stirred solution of DMSO (0.92 mL, 12.87 mmol) in dry DCM (40 mL) at −78° C. and the reaction mixture was stirred for 15 minutes. Compound 22 (1 g, 4.29 mmol) dissolved in DCM (15 mL) was the added drop-wise and the reaction mixture was stirred at −78° C. for 1 hour. The reaction mixture was then quenched by adding Et3N (2.9 mL, 21.45 mmol) drop-wise and the solution was stirred at rt for 15 minutes. Water was then added to the solution and the reaction mixture was extracted with DCM. The organic layer was dried over Na2SO4, filtered and concentrated to yield crude compound 23 which was used as such for the next step. the reaction mixture was stirred at −78° C. for 1 hour The reaction mixture was then quenched the solution was stirred at rt for 15 minutes the reaction mixture was extracted with DCM The organic layer was dried over Na2SO4 filtered concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Oxalyl chloride (0.55 mL, 6.44 mmol) was added to a stirred solution of DMSO (0.92 mL, 12.87 mmol) in dry DCM (40 mL) at −78° C. and the reaction mixture was stirred for 15 minutes. Compound 22 (1 g, 4.29 mmol) dissolved in DCM (15 mL) was the added drop-wise and the reaction mixture was stirred at −78° C. for 1 hour. The reaction mixture was then quenched by adding Et3N (2.9 mL, 21.45 mmol) drop-wise and the solution was stirred at rt for 15 minutes. Water was then added to the solution and the reaction mixture was extracted with DCM. The organic layer was dried over Na2SO4, filtered and concentrated to yield crude compound 23 which was used as such for the next step. the reaction mixture was stirred at −78° C. for 1 hour The reaction mixture was then quenched the solution was stirred at rt for 15 minutes the reaction mixture was extracted with DCM The organic layer was dried over Na2SO4 filtered concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a stirred solution of compound 21 (3 g, 16.71 mmol) in ethanol (23 mL) was added K2CO3 (11.5 g, 83.55 mmol) portion-wise at ice cold conditions. Benzyl bromide (2 mL, 16.71 mmol) was then added and the reaction mixture was heated at reflux for 2 hours. The reaction mixture was filtered, and washed with EtOAc. The filtrate was concentrated, the residue was dissolved in EtOAc, washed with saturated NaHCO3 solution and brine, dried over Na2SO4, filtered and concentrated. The crude material was purified by 230-400 silica gel column chromatography using 1-3% MeOH-DCM as eluent to yield compound 22. the reaction mixture was heated at reflux for 2 hours The reaction mixture was filtered washed with EtOAc The filtrate was concentrated the residue was dissolved in EtOAc washed with saturated NaHCO3 solution and brine dried over Na2SO4 filtered concentrated The crude material was purified by 230-400 silica gel column chromatography

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Oxalyl chloride (0.55 mL, 6.44 mmol) was added to a stirred solution of DMSO (0.92 mL, 12.87 mmol) in dry DCM (40 mL) at −78° C. and the reaction mixture was stirred for 15 minutes. Compound 22 (1 g, 4.29 mmol) dissolved in DCM (15 mL) was the added drop-wise and the reaction mixture was stirred at −78° C. for 1 hour. The reaction mixture was then quenched by adding Et3N (2.9 mL, 21.45 mmol) drop-wise and the solution was stirred at rt for 15 minutes. Water was then added to the solution and the reaction mixture was extracted with DCM. The organic layer was dried over Na2SO4, filtered and concentrated to yield crude compound 23 which was used as such for the next step. the reaction mixture was stirred at −78° C. for 1 hour The reaction mixture was then quenched the solution was stirred at rt for 15 minutes the reaction mixture was extracted with DCM The organic layer was dried over Na2SO4 filtered concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a stirred solution of compound 21 (3 g, 16.71 mmol) in ethanol (23 mL) was added K2CO3 (11.5 g, 83.55 mmol) portion-wise at ice cold conditions. Benzyl bromide (2 mL, 16.71 mmol) was then added and the reaction mixture was heated at reflux for 2 hours. The reaction mixture was filtered, and washed with EtOAc. The filtrate was concentrated, the residue was dissolved in EtOAc, washed with saturated NaHCO3 solution and brine, dried over Na2SO4, filtered and concentrated. The crude material was purified by 230-400 silica gel column chromatography using 1-3% MeOH-DCM as eluent to yield compound 22. the reaction mixture was heated at reflux for 2 hours The reaction mixture was filtered washed with EtOAc The filtrate was concentrated the residue was dissolved in EtOAc washed with saturated NaHCO3 solution and brine dried over Na2SO4 filtered concentrated The crude material was purified by 230-400 silica gel column chromatography