Реакция #333833

Уравнение реакции

Me3Al

tert-butyl 4-(tert-butylsulfinylimino)cyclohexylcarbamate

MeLi

dimethoxymethane

→

tert-butyl 4-(1,1-dimethylethylsulfinamido)-4-methylcyclohexylcarbamate

Выход 33.0%

Растворители

toluene

toluene

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe reaction mixture was stirred at −78° C. for 4 hours
2. 2
   ДругоеThe reaction was quenched
3. 3
   workup.ADDITIONby adding 2 mL of water
4. 4
   Другоеthe solvents evaporated under reduced pressure
5. 5
   Промывкаeluting with a mixture of petroleum ether and ethyl acetate (4:1

Методика

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.

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