Réaction #632007

Équation de réaction

n-butyllithium

methyl iodide

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

n-butyllithium

→

desired product

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

Solvants

THF

Conditions de réaction

Traitement

1. 1
   AutreThe dry ice bath was removed
2. 2
   Températurethe reaction mixture was warmed to room temperature over a period of 1.5 hours
3. 3
   TempératureThis mixture was cooled to −78° C.
4. 4
   TempératureThe reaction mixture was warmed to room temperature
5. 5
   Températurecooled to −78° C. over a period of 2 hours
6. 6
   TempératureThe reaction mixture was warmed to room temperature overnight
7. 7
   Autrequenched with saturated NH4Cl (100 mL) at room temperature
8. 8
   Extractionextracted with ethyl acetate (100 mL)
9. 9
   LavageThe organic phase was washed with brine (100 mL)
10. 10
    Séchagedried (MgSO4)
11. 11
    Filtrationfiltered
12. 12
    Concentrationconcentrated in vacuo
13. 13
    Autreto provide a yellow oil which
14. 14
    Autrewas crystallized from hexane

Mode opératoire

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).

Source