Trimethylaluminum → Tert-butyl 3-(1,1-dimethylethylsulfinamido)-3-methylcyclobutylcarbamate
Reaction equation
[C:1]([S:5]([N:7]=[C:8]1[CH2:11][CH:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:9]1)=[O:6])([CH3:4])([CH3:3])[CH3:2].[CH3:20][Al](C)C.[Li]C>C1(C)C=CC=CC=1>[CH3:2][C:1]([CH3:4])([S:5]([NH:7][C:8]1([CH3:20])[CH2:11][CH:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:9]1)=[O:6])[CH3:3]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
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.
Workup
- stirringThe reaction mixture was stirred at −78° C. for additional 4 hours
- customwas then quenched
- additionby adding 3 mL of water
- customThe solvent was removed under reduced pressure
- washeluting with a mixture of petroleum ether and ethyl acetate (4:1
Sources & evidence
- ORD record
- ord-f09750dfdd53449184b23a05b8ce93c4
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658646B2
Reaction notes
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