تفاعل #1884967

معادلة التفاعل

n-butyl lithium

3-chloropropylsulfonylamine tert-butylcarbamate

→

cyclopropylsulfonylamine tert-butyl carbamate

المردود 100.0%

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe dry ice bath was removed
2. 2
   درجة الحرارةto warm to room temperature over a period of 2 hours
3. 3
   أخرىThe reaction mixture was quenched with glacial acetic acid (3.4 mL)
4. 4
   تركيزconcentrated in vacuo
5. 5
   أخرىpartitioned between dichloromethane (100 mL) and water (100 mL)
6. 6
   غسيلThe organic phase was washed with brine (100 mL)
7. 7
   تجفيفdried (MgSO4)
8. 8
   ترشيحfiltered
9. 9
   تركيزconcentrated in vacuo

الإجراء التجريبي

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.

المصدر