HCID 178418373, compound → HCID 178468181, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of tert-butyl cis-4-(methoxy(methyl)carbamoyl)cyclohexylcarbamate (4.7 g, 16.41 mmol) in THF (109 mL) was cooled to 0° C. under nitrogen atmosphere. To this was added methylmagnesium iodide (3M in ether solution)(10.94 mL, 32.8 mmol) dropwise via syringe, and the mixture was stirred at 0° C. for 1 hour. The ice bath was removed, and the reaction mixture was stirred for 18 hours at RT. The reaction mixture was again cooled to 0° C. under nitrogen atmosphere and quenched with aqueous NH4Cl (100 mL). DCM (200 mL) was added, and the layers were separated. The organic layer was washed with brine (30 mL), dried over sodium sulfate and concentrated to afford a yellow oil which was purified by silica gel chromatography (5-30% MeOH/DCM) to afford tert-butyl cis-4-acetylcyclohexylcarbamate as an off-white solid (1.8 g, 45.4% yield).

Provenance & Evidence