反应 #632011

反应方程式

n-butyllithium

3-chloropropylsulfonylamine tert-butylcarbamate

→

desired product

收率 100.0%

Cyclopropylsulfonylamine Tert-Butyl Carbamate

收率 100.0%

溶剂

THF

THF

反应条件

后处理

1. 1
   其他The dry ice bath was removed
2. 2
   温度to warm to room temperature over a period of 2 hours
3. 3
   其他The reaction mixture was quenched with glacial acetic acid (3.4 mL)
4. 4
   浓缩concentrated in vacuo
5. 5
   其他partitioned between dichloromethane (100 mL) and water (100 mL)
6. 6
   洗涤The organic phase was washed with brine (100 mL)
7. 7
   干燥dried (MgSO4)
8. 8
   过滤filtered
9. 9
   浓缩concentrated in vacuo

实验过程

A solution of n-butyllithium (74.7 mL, 119.5 mmol, 1.6M in hexane) was dissolved in dry THF (105 mL) and cooled to −78° C. under an argon atmosphere. To this solution was added a solution of 3-chloropropylsulfonylamine tert-butylcarbamate (14 g, 54.3 mmol) in dry THF (105 mL) dropwise over 20-30 minutes. The dry ice bath was removed and the reaction mixture was allowed to warm to room temperature over a period of 2 hours. The reaction mixture was quenched with glacial acetic acid (3.4 mL), concentrated in vacuo, and partitioned between dichloromethane (100 mL) and water (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO4), filtered, and concentrated in vacuo to provide the desired product as a waxy off-white solid (12.08 g, 100%): 1H NMR (CDCl3) δ 1.10 (m, 2H), 1.34 (m, 2H), 1.50 (s, 9H), 2.88 (m, 1H), 7.43 (s, 1H). 13C NMR (CDCl3) δ 6.21, 28.00, 31.13, 84.07, 149.82.

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