反応 #632011

反応方程式

n-butyllithium

3-chloropropylsulfonylamine tert-butylcarbamate

→

desired product

収率 100.0%

Cyclopropylsulfonylamine Tert-Butyl Carbamate

収率 100.0%

溶媒

THF

THF

反応条件

後処理

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

実験手順

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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