Acetic Acid → HCID 67071602, compound

Participants

Reaction Steps

(−)-(E)-3-[4-Oxo-spiro(chromane-2,3′-piperidine)-6-yl]-acrylic acid methyl ester hydrochloride (505 mg, 1.49 mmol) was suspended in DCM (50 ml). TEA (0.208 ml, 1.49 mmol) was added and the pH was adjusted to 5 with AcOH. Benzaldehyde (190 mg, 1.794 mmol) and NaBH(OAc)3 (475 mg, 2.24 mmol) were added and the mixture was stirred at RT for 3 h. The resulting solution was washed with 5% NaHCO3 and brine, then dried over Na2SO4 and evaporated to dryness. The crude product was purified by column chromatography (eluent:petroleum ether:EtOAc 9:1 to 7:3) to give (−)-(E)-3-[1′-benzyl-4-oxo-spiro(chromane-2,3′-piperidine)-6-yl]-acrylic acid methyl ester (547 mg).

Provenance & Evidence