2,6-Dimethylcyclohexanol → HCID 117642487, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (60 wt % in oil) (78 mg, 1.95 mmol) was added to a stirred solution of 2,6-dimethylcyclohexanol (250 mg, 1.95 mmol) in DMF (1.95 mL). The mixture was heated at 60° C. for 10 min and then ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (6) (206 mg, 0.39 mmol) was added in one portion. The reaction was allowed to stir at 70° C. for 16 h. The cooled reaction mixture was filtered through Celite, and the filtrate diluted with EtOAc (20 mL) and washed with water (3×10 mL), the organic layer was dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography (12 g, 0.5% MeOH (1% NH3) in DCM) to afford 2,6-dimethylcyclohexyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (45) (73 mg, 20%) as a brown oil. m/z 611 (M+H)+ (ES+)

Provenance & Evidence