Reaction #632006

Reaction equation

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

n-butyllithium

→

desired product

Yield 56.4%

Cyclopropanesulfonic Acid Tert-Butylamide

Yield 56.4%

Solvents

THF

Conditions

Workup

1. 1
   Concentrationconcentrated in vacuo
2. 2
   OtherThe concentrate was partitioned between ethyl acetate and water (200 mL, 200 mL)
3. 3
   WashThe organic phase was washed with brine
4. 4
   Dryingdried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated in vacuo
7. 7
   OtherThe concentrate 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-butyllithium (2.5M in hexane, 8.0 mL, 20.0 mmol) at −78° C. The reaction mixture was warmed to room temperature over a period of 1 hour and concentrated in vacuo. The concentrate was partitioned between ethyl acetate and water (200 mL, 200 mL). The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The concentrate was recrystallized from hexane to provide the desired product as a white solid (1.0 g, 56%). 1H NMR (CDCl3) δ 0.98-1.00 (m, 2H), 1.18-1.19 (m, 2H), 1.39 (s, 9H), 2.48-2.51 (m, 1H), 4.19 (br, 1H).

Source