Hydrochloric Acid → HCID 178468185, compound

Participants

Reaction Conditions

Reaction Steps

Cis-4-(benzyloxy)-N-methoxy-N-methylcyclohexanecarboxamide (1.3 g, 4.7 mmol) was dissolved in THF (10 mL). CH3Li (3.0 M solution in diethoxymethane, 8.0 mL, 14.1 mmol, 3.0 eq.) was added to the solution dropwise at −70° C. The mixture was stirred at −70° C. under nitrogen atmosphere for 1 h. then 1 M HCl solution was added to the mixture until pH=6. The mixture was extracted with ethyl acetate and the organic layer was concentrated and purified by silica gel column chromatography using petroleum ether/ethyl acetate (3/1) as eluent to give product as a slight yellow oil (720 mg, 60%). 1H NMR (400 MHz, CDCl3) δ 7.34-7.25 (m, 5H), 4.49 (s, 2H), 3.62-3.60 (m, 1H), 2.40-2.25 (m, 1H), 2.13 (s, 3H), 1.97-1.93 (m, 2H), 1.86-1.80 (m, 2H), 1.67-1.54 (m, 2H), 1.53-1.47 (m, 2H).

Provenance & Evidence