Reacción #632011

Ecuación de reacción

n-butyllithium

3-chloropropylsulfonylamine tert-butylcarbamate

→

desired product

Rendimiento 100.0%

Cyclopropylsulfonylamine Tert-Butyl Carbamate

Rendimiento 100.0%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe dry ice bath was removed
2. 2
   Temperaturato warm to room temperature over a period of 2 hours
3. 3
   OtroThe reaction mixture was quenched with glacial acetic acid (3.4 mL)
4. 4
   Concentraciónconcentrated in vacuo
5. 5
   Otropartitioned between dichloromethane (100 mL) and water (100 mL)
6. 6
   LavadoThe organic phase was washed with brine (100 mL)
7. 7
   Secadodried (MgSO4)
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated in vacuo

Procedimiento

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.

Fuente