Réaction #632011

Équation de réaction

n-butyllithium

3-chloropropylsulfonylamine tert-butylcarbamate

→

desired product

Rendement 100.0%

Cyclopropylsulfonylamine Tert-Butyl Carbamate

Rendement 100.0%

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   AutreThe dry ice bath was removed
2. 2
   Températureto warm to room temperature over a period of 2 hours
3. 3
   AutreThe reaction mixture was quenched with glacial acetic acid (3.4 mL)
4. 4
   Concentrationconcentrated in vacuo
5. 5
   Autrepartitioned between dichloromethane (100 mL) and water (100 mL)
6. 6
   LavageThe organic phase was washed with brine (100 mL)
7. 7
   Séchagedried (MgSO4)
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated in vacuo

Mode opératoire

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.

Source