Dimethoxymethane → Tert-butyl 4-(1,1-dimethylethylsulfinamido)-4-methylcyclohexylcarbamate
Reaction equation
[C:1]([S:5]([N:7]=[C:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:10][CH2:9]1)=[O:6])([CH3:4])([CH3:3])[CH3:2].[CH3:22][Al](C)C.[Li]C.COCOC>C1(C)C=CC=CC=1>[CH3:2][C:1]([CH3:4])([S:5]([NH:7][C:8]1([CH3:22])[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:10][CH2:9]1)=[O:6])[CH3:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
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.
Workup
- stirringthe reaction mixture was stirred at −78° C. for 4 hours
- customThe reaction was quenched
- additionby adding 2 mL of water
- customthe solvents evaporated under reduced pressure
- washeluting with a mixture of petroleum ether and ethyl acetate (4:1
Sources & evidence
- ORD record
- ord-393e3df14e62464784dbdb514a2cff34
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658646B2
Reaction notes
Loading…