tert-Butyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamate → tert-butyl N-(2-cyclohexyl-2-oxoethyl)carbamate
Reaction equation
CON(C)[C:4](=[O:14])[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[CH:16]1([Mg]Cl)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>C1COCC1>[CH:16]1([C:4](=[O:14])[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:11])[CH3:12])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1Participants
4
Procedure
To a tert-butyl 2-(methoxy(methyl)amino)-2-oxoethylcarbamate (400 mg, 1.83 mmol) in THF (10 mL) was added cyclohexylmagnesium chloride (4.12 mL, 8.24 mmol) portionwise at room temperature under N2 atmosphere. As addition of the Grignard reagent was completed, the reaction mixture was stirred and heated to reflux for an hour. Then the mixture was allowed to cool down to room temperature. The reaction was quenched by adding water (10 mL) slowly. 1N HCl solution (30 mL) was added to the mixture, and extracted with EtOAc (20 mL×3). The combined organic layers were collected and evaporated in vacuo. The crude material was purified by column chromatography (hexane: EtOAc=10:1 to 5:1) to yield the desired product (110 mg, 25%).