Reacción #1884964

Ecuación de reacción

methyl iodide

n-BuLi

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

n-BuLi

→

solid

Rendimiento 81.0%

N-tert-Butyl-(1-methyl)cyclopropylsulfonamide

Rendimiento 81.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe dry ice bath was removed
2. 2
   Temperaturato warm to rt over a period of 1.5 h
3. 3
   TemperaturaThis mixture was then cooled to −78° C.
4. 4
   TemperaturaThe reaction mixture was warmed to rt
5. 5
   Temperaturato warm to rt overnight
6. 6
   Otroquenched with saturated NH4Cl (100 mL) at rt
7. 7
   ExtracciónIt was extracted with EtOAc (100 mL)
8. 8
   LavadoThe organic phase was washed with brine (100 mL)
9. 9
   Secadodried (MgSO4)
10. 10
    Concentraciónconcentrated in vacuo
11. 11
    Otroto give a yellow oil which
12. 12
    Otrowas crystallized from hexane

Procedimiento

A solution of N-tert-butyl-(3-chloro)propylsulfonamide (4.3 g, 20 mmol) was dissolved in dry THF (100 mL) and cooled to −78° C. To this solution was added n-BuLi (17.6 mL, 44 mmol, 2.5 M in hexane) slowly. The dry ice bath was removed and the reaction mixture was allowed to warm to rt over a period of 1.5 h. This mixture was then cooled to −78° C., and a solution of n-BuLi (20 mmol, 8 mL, 2.5 M in hexane) was added. The reaction mixture was warmed to rt, recooled to −78° C. over a period of 2 h and a neat solution of methyl iodide (5.68 g, 40 mmol) added. The reaction mixture was allowed to warm to rt overnight, quenched with saturated NH4Cl (100 mL) at rt. It was extracted with EtOAc (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO4), and concentrated in vacuo to give a yellow oil which was crystallized from hexane to afford the product as a slightly yellow solid (3.1 g, 81%): 1H NMR (CDCl3) δ 0.79 (m, 2H), 1.36 (s, 9H), 1.52 (m, 2H), 1.62 (s, 3H), 4.10 (bs, 1H).

Fuente