تفاعل #5190

معادلة التفاعل

sodium hydroxide

sodium chloride

formalin

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

sodium cyanoborohydride

→

title compound

المردود 55.5%

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

المردود 55.5%

المذيبات

acetonitrile

acetic acid

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONadded to the mixture over a period of 5 minutes
2. 2
   درجة الحرارةAt 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
   استخلاصafter which it was extracted with ethyl acetate
5. 5
   غسيلThe extract was washed with an aqueous solution of sodium chloride
6. 6
   تجفيفdried over anhydrous magnesium sulfate
7. 7
   أخرىThe solvent was then removed by distillation under reduced pressure
8. 8
   أخرىthe residue was purified by a similar procedure to
9. 9
   أخرىthat described in Preparation 4-(10)

الإجراء التجريبي

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).

المصدر