Реакция #1884967

Уравнение реакции

n-butyl lithium

3-chloropropylsulfonylamine tert-butylcarbamate

→

cyclopropylsulfonylamine tert-butyl carbamate

Выход 100.0%

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   ДругоеThe dry ice bath was removed
2. 2
   Температураto warm to room temperature over a period of 2 hours
3. 3
   ДругоеThe reaction mixture was quenched with glacial acetic acid (3.4 mL)
4. 4
   Концентрированиеconcentrated in vacuo
5. 5
   Другоеpartitioned between dichloromethane (100 mL) and water (100 mL)
6. 6
   ПромывкаThe organic phase was washed with brine (100 mL)
7. 7
   Сушкаdried (MgSO4)
8. 8
   Фильтрацияfiltered
9. 9
   Концентрированиеconcentrated in vacuo

Методика

A solution of n-butyl lithium (74.7 mL, 119.5 mmol, 1.6M in hexane) was dissolved in dry THF (105 mL) and cooled to −78° C. under a 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 afford the cyclopropylsulfonylamine tert-butyl carbamate 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.

Источник