Ammonia → HCID 67071602, compound

Participants

Reaction Steps

A suspension of Intermediate 2 (400 mg, 1.19 mmol) in NaHCO3 (10% aqueous solution) was extracted 3 times with DCM (10 ml). The organic phase was dried over Na2SO4 and evaporated. The resulting oil was dissolved in DCM (10 ml), treated with benzaldehyde (0.145 ml, 1.42 mmol) and NaBH(OAc)3 (383 mg, 1.78 mmol), and the resulting clear solution was stirred at RT for 2 h. Water was added to the mixture and the pH was adjusted to a basic value with NH3. The mixture was extracted 3 times with DCM (10 ml). The organic layer was dried, evaporated, and the crude residue was purified by column chromatography (eluent: DCM:MeOH 98:2) to give (±)-(E)-3-[1′-benzyl-4-oxo-spiro(chromane-2,3′-piperidine)-6-yl]-acrylic acid methyl ester (300 mg) as a light yellow solid.

Provenance & Evidence