반응 #5190

반응 방정식

sodium hydroxide

sodium chloride

formalin

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

sodium cyanoborohydride

→

title compound

수율 55.5%

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

수율 55.5%

용매

acetonitrile

acetic acid

반응 조건

후처리

1. 1
   workup.ADDITIONadded to the mixture over a period of 5 minutes
2. 2
   온도At 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
   추출after which it was extracted with ethyl acetate
5. 5
   세척The extract was washed with an aqueous solution of sodium chloride
6. 6
   건조dried over anhydrous magnesium sulfate
7. 7
   기타The solvent was then removed by distillation under reduced pressure
8. 8
   기타the residue was purified by a similar procedure to
9. 9
   기타that described in Preparation 4-(10)

실험 절차

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).

출처