反应 #1178477

反应方程式

(S)-1-(tert-butoxycarbonyl)-2-azetidinecarboxylic acid

→

title compound

收率 87.0%

(S)-1-(tert-butoxycarbonyl)azetidine-2-methanol

收率 87.0%

溶剂

tetrahydrofuran

tetrahydrofuran

反应条件

后处理

1. 1
   workup.DISSOLUTIONto dissolve the compound
2. 2
   温度the mixture was heated
3. 3
   温度to reflux for 2 hours
4. 4
   workup.WAITThe reaction solution was left
5. 5
   温度to cool
6. 6
   浓缩was concentrated under reduced pressure
7. 7
   workup.ADDITIONIce water (100 mL) was poured
8. 8
   萃取the mixture was extracted with ethyl acetate (200 mL×2)
9. 9
   洗涤The extract was washed with saturated brine (200 mL)
10. 10
    干燥dried over anhydrous sodium sulfate
11. 11
    过滤After filtering the extract
12. 12
    浓缩the filtrate was concentrated under reduced pressure

实验过程

(S)-1-(tert-butoxycarbonyl)-2-azetidinecarboxylic acid (10.42 g, 49.4 mmol) was introduced into a 500-mL pear-shaped flask, and tetrahydrofuran (200 mL) was added to dissolve the compound. Then, a tetrahydrofuran solution of 10 M borane-dimethyl sulfide complex salt (9.87 mL, 98.7 mmol) was slowly added at 0° C., and the mixture was heated to reflux for 2 hours while stirring. The reaction solution was left to cool, and then was concentrated under reduced pressure. Ice water (100 mL) was poured thereto, and the mixture was extracted with ethyl acetate (200 mL×2). The extract was washed with saturated brine (200 mL), and then dried over anhydrous sodium sulfate. After filtering the extract, the filtrate was concentrated under reduced pressure to obtain the title compound (8.03 g, 42.9 mmol, 87%) as an oily matter.

来源