تفاعل #42282

معادلة التفاعل

Sodium borohydride

tert-Butyl (1S)-3-bromo-1-(3,5-difluorobenzyl)-2-oxopropylcarbamate

→

title compound

tert-Butyl (1S,2S)-3-bromo-1-(3,5-difluorobenzyl)-2-hydroxypropylcarbamate

المذيبات

ethyl acetate hexane

—

alcohol

ظروف التفاعل

المعالجة

1. 1
   أخرىThe mixture is quenched with water (10 mL)
2. 2
   أخرىthe solvent removed under reduced pressure
3. 3
   درجة الحرارةwith heat (not
4. 4
   أخرىexceeding 30 degrees C
5. 5
   أخرىThe solid is partitioned between dichloromethane and water
6. 6
   غسيلwashed with saline
7. 7
   تجفيفdried over anhydrous sodium sulfate
8. 8
   أخرىThe solvent is removed under reduced pressure

الإجراء التجريبي

Sodium borohydride (1.32 g, 34.9 mmole, 1.1 eq.) is added to tert-Butyl (1S)-3-bromo-1-(3,5-difluorobenzyl)-2-oxopropylcarbamate (III, EXAMPLE 1, 12 g, 31.75 mmole) dissolved in absolute alcohol (500 mL) at −78 degrees C. The reaction mixture is stirred for 0.5 hour and monitored by TLC (ethyl acetate/hexane, 20/80; Rf=0.2). The mixture is quenched with water (10 mL) and the solvent removed under reduced pressure with heat (not exceeding 30 degrees C.) to dryness. The solid is partitioned between dichloromethane and water, washed with saline, dried over anhydrous sodium sulfate. The solvent is removed under reduced pressure to give the title compound, TLC (ethyl acetate/hexane, 20/80) Rf=0.2; MS (MH+)=381.2.

المصدر