Reacción #632007

Ecuación de reacción

n-butyllithium

methyl iodide

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

n-butyllithium

→

desired product

N-tert-butyl-(1-methyl)cyclopropyl-sulfonamide

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe dry ice bath was removed
2. 2
   Temperaturathe reaction mixture was warmed to room temperature over a period of 1.5 hours
3. 3
   TemperaturaThis mixture was cooled to −78° C.
4. 4
   TemperaturaThe reaction mixture was warmed to room temperature
5. 5
   Temperaturacooled to −78° C. over a period of 2 hours
6. 6
   TemperaturaThe reaction mixture was warmed to room temperature overnight
7. 7
   Otroquenched with saturated NH4Cl (100 mL) at room temperature
8. 8
   Extracciónextracted with ethyl acetate (100 mL)
9. 9
   LavadoThe organic phase was washed with brine (100 mL)
10. 10
    Secadodried (MgSO4)
11. 11
    Filtraciónfiltered
12. 12
    Concentraciónconcentrated in vacuo
13. 13
    Otroto provide a yellow oil which
14. 14
    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-butyllithium (17.6 mL, 44 mmol, 2.5M in hexane) slowly. The dry ice bath was removed and the reaction mixture was warmed to room temperature over a period of 1.5 hours. This mixture was cooled to −78° C. and a solution of n-butyllithium (20 mmol, 8 mL, 2.5M in hexane) was added. The reaction mixture was warmed to room temperature, cooled to −78° C. over a period of 2 hours, and treated with a neat solution of methyl iodide (5.68 g, 40 mmol). The reaction mixture was warmed to room temperature overnight, then quenched with saturated NH4Cl (100 mL) at room temperature and extracted with ethyl acetate (100 mL). The organic phase was washed with brine (100 mL), dried (MgSO4), filtered, and concentrated in vacuo to provide a yellow oil which was crystallized from hexane to provide the desired 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 (br s, 1H).

Fuente