(3-Cyclohexylcarbamoylmethyl-phenyl)-acetic acid → 2-[3-(2-Cyclohexylamino-ethyl)-phenyl]-ethanol

Participants

Reaction Steps

(3-Cyclohexylcarbamoylmethyl-phenyl)-acetic acid (620 mg) was dissolved in dry dichloromethane (25 mL) and treated with borane-methyl sulphide complex (2M, 12 mL) at room temperature. The reaction was stirred at room temperature for 1 hour and at reflux for a further 1 hour. The mixture was cooled, quenched with methanol and treated with 2M hydrochloric acid (25 mL). The acidified mixture was heated at reflux for 10 minutes, cooled and basified with 2M sodium hydroxide. The basic mixture was extracted with dichloromethane (2×50 mL). The organic extracts were combined, dried over anhydrous sodium sulphate, filtered and concentrated to yield 500 mg of the sub-titled compound as an oil.

Provenance & Evidence