反应 #5190

反应方程式

sodium hydroxide

sodium chloride

formalin

(2S, 4S)-4-(4-methoxybenzylthio)-2-methoxycarbonylpyrrolidine

sodium cyanoborohydride

→

title compound

收率 55.5%

(2S, 4S)-4-(4-Methoxybenzylthio)-2-methoxycarbonyl-1-methylpyrrolidine

收率 55.5%

溶剂

acetonitrile

acetic acid

反应条件

后处理

1. 1
   workup.ADDITIONadded to the mixture over a period of 5 minutes
2. 2
   温度At the end of this time, the mixture was cooled
3. 3
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 40 minutes
4. 4
   萃取after which it was extracted with ethyl acetate
5. 5
   洗涤The extract was washed with an aqueous solution of sodium chloride
6. 6
   干燥dried over anhydrous magnesium sulfate
7. 7
   其他The solvent was then removed by distillation under reduced pressure
8. 8
   其他the residue was purified by a similar procedure to
9. 9
   其他that described in Preparation 4-(10)

实验过程

3.43 ml of 35% formalin were added to a solution of 2.25 g of (2S, 4S)-4-(4-methoxybenzylthio)-2-methoxycarbonylpyrrolidine dissolved in 42 ml of acetonitrile. Subsequently, 804 mg of sodium cyanoborohydride were divided into three portions and added to the mixture over a period of 5 minutes. The mixture was then stirred at room temperature for 30 minutes. At the end of this time, the mixture was cooled, 1.3 ml of acetic acid was added, and the reaction mixture was stirred at room temperature for 40 minutes. 40 ml of a 1N aqueous solution of sodium hydroxide and an aqueous solution of sodium chloride were then added to the mixture, after which it was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was purified by a similar procedure to that described in Preparation 4-(10), to afford 1.31 g of the title compound as an oil. The infra-red spectrum, nuclear magnetic resonance spectrum and thin layer chromatograph of this compound were identical to those of the compound prepared as described in Preparation 4-(10).

来源