Acetic Acid → HCID 69557956, compound

Participants

Reaction Steps

To a solution of 1-((SR)-(benzyloxycarbonylamino)-3-(SR)-(formyl)-4-(SR)-phenylcyclopentane (from Step F, derived from Higher Rf isomer in Step D) (450 mg, 0.1.4 mmol) in 1,2-dichloroethane (10 mL) was added 4-(3-phenylprop-1-yl)piperidine (424 mg, 2.1 mmol) and acetic acid (0.125 mL, 2.1 mmol). After 15 min, sodium triacetoxyborohydride (890 mg, 4.2 mmol) was added in portions over 30 min and the reaction was stirred at RT for 16 h. The reaction was diluted with methylene chloride, quenched with aq. sodium carbonate and extracted 3 times with methylene chloride. The organic layers were each washed with brine, dried over sodium sulfate, combined and concentrated in vacuo. The residue was purified by FC (30-40% ethyl acetate in hexanes) to give the title product (698 mg) as the free amine.

Provenance & Evidence