Réaction #632006

Équation de réaction

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

n-butyllithium

→

desired product

Rendement 56.4%

Cyclopropanesulfonic Acid Tert-Butylamide

Rendement 56.4%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Concentrationconcentrated in vacuo
2. 2
   AutreThe concentrate was partitioned between ethyl acetate and water (200 mL, 200 mL)
3. 3
   LavageThe organic phase was washed with brine
4. 4
   Séchagedried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated in vacuo
7. 7
   AutreThe concentrate was recrystallized from hexane

Mode opératoire

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