Dimethoxymethane → Tert-butyl 4-(1,1-dimethylethylsulfinamido)-4-methylcyclohexylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of tert-butyl 4-(tert-butylsulfinylimino)cyclohexylcarbamate (0.6 g, 1.9 mmol) in 40 mL of toluene at −78° C. was added, under a nitrogen atmosphere, a solution of Me3Al 2M in toluene (2 mL, 4 mmol). The mixture was stirred for 20 minutes at −78° C., then a solution of MeLi, 3M in dimethoxymethane (2.8 mL, 8.4 mmol), was added slowly and the reaction mixture was stirred at −78° C. for 4 hours. The reaction was quenched by adding 2 mL of water and the solvents evaporated under reduced pressure. 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 4-(1,1-dimethylethylsulfinamido)-4-methylcyclohexylcarbamate (0.21 g, 33%) as crude yellow oil which was used for the next step without further purification. MS: (M+H)+=333.2.

Provenance & Evidence