Trimethylaluminum → Tert-butyl 3-(1,1-dimethylethylsulfinamido)-3-methylcyclobutylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of tert-butyl 3-(tert-butylsulfinylimino)cyclobutylcarbamate (0.8 g, 2.8 mmol) in 60 mL of toluene at −78° C. was added Me3Al (3.1 mL, 6.2 mmol, 2M in toluene). After stirred 20 minutes at −78° C., MeLi (4.1 mL, 12.3 mmol, 3M in dimethoxymethane) was added slowly. The reaction mixture was stirred at −78° C. for additional 4 hours, and was then quenched by adding 3 mL of water. The solvent was removed under reduced pressure and the residue was passed through a pad of silica gel (200-300 mesh, eluting with a mixture of petroleum ether and ethyl acetate (4:1, v/v) to give tert-butyl 3-(1,1-dimethylethylsulfinamido)-3-methylcyclobutylcarbamate (0.45 g, 53%) as a crude oil which was used for the next step without further purification. MS: (M+H)+=305.2.

Provenance & Evidence