Reacción #1884963

ord-feb3d9d0a6174fd686704936a68f14cb

Ecuación de reacción

CC(C)(C)NS(=O)(=O)CCCCl
N-tert-butyl-(3-chloro)propylsulfonamide
[Li][CH2]CCC
n-BuLi
CC(C)(C)NS(=O)(=O)C1CC1
desired product
Rendimiento 56.4%
CC(C)(C)NS(=O)(=O)C1CC1
Cyclopropanesulfonic Acid tert-Butylamide
Rendimiento 56.4%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe volatiles were removed in vacuo
  2. 2
    OtroThe residue was partitioned between EtOAC and water (200 mL, 200 mL)
  3. 3
    LavadoThe separated organic phase was washed with brine
  4. 4
    Secadodried over Na2SO4
  5. 5
    Filtraciónfiltered
  6. 6
    Concentraciónconcentrated in vacuo
  7. 7
    OtroThe residue was recrystallized from hexane

Procedimiento

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%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08343477B2uspto-grants-2013_01