Reaction #1884963

Reaction equation

N-tert-butyl-(3-chloro)propylsulfonamide

n-BuLi

→

desired product

Yield 56.4%

Cyclopropanesulfonic Acid tert-Butylamide

Yield 56.4%

Solvents

THF

Conditions

Workup

1. 1
   OtherThe volatiles were removed in vacuo
2. 2
   OtherThe residue was partitioned between EtOAC and water (200 mL, 200 mL)
3. 3
   WashThe separated organic phase was washed with brine
4. 4
   Dryingdried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated in vacuo
7. 7
   OtherThe residue was recrystallized from hexane

Procedure

To a solution of N-tert-butyl-(3-chloro)propylsulfonamide (2.14 g, 10.0 mmol) in THF (100 mL) was added n-BuLi (2.5 M in hexane, 8.0 mL, 20.0 mmol) at −78° C. The reaction mixture was allowed to warm up to room temperature over period of 1 h. The volatiles were removed in vacuo. The residue was partitioned between EtOAC and water (200 mL, 200 mL). The separated organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was recrystallized from hexane to yield the desired product as a white solid (1.0 g, 56%).

Source