Ammonia → HCID 67071573, compound

Participants

Reaction Steps

A suspension of (±)-(E)-3-[4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-acrylic acid methyl ester hydrochloride salt (440 mg, 1.36 mmol, Intermediate 1) in aqueous 10% NaHCO3 solution was extracted with DCM (3×10 ml). The organic phase was dried over Na2SO4 and evaporated. The resulting oil was dissolved in DCM (15 ml), treated with benzaldehyde (0.166 ml, 1.63 mmol) and NaBH(OAc)3 (433 mg, 2.04 mmol), and the resulting clear solution was stirred at RT for 2 h. Water was added to the mixture and the pH was brought to basic conditions with NH3. The mixture was extracted with DCM (3×10 ml). The organic layer was dried, evaporated, and the crude residue was purified by column chromatography (eluent: petroleum ether/EtOAc 7:3) to give (±)-(E)-3-[1′-benzyl-4-oxo-spiro(chromane-2,3′-pyrrolidine)-6-yl]-acrylic acid methyl ester (482 mg) as a light yellow solid.

Provenance & Evidence