Acetic Acid → HCID 68537233, compound

Participants

Reaction Steps

1-(Methylcarbonyloxy-methyl)-spiro[indoline-3,4′-piperidin]-2-one (0.026 g, 0.095 mmol) and 4-chloro-benzaldehyde (0.02 g, 0.14 mmol) were dissolved in dry 1,2-dichloroethane (1.5 mL). To the reaction mixture was then added glacial acetic acid (0.006 g, 0.095 mmol) under nitrogen atmosphere and the reaction mixture was stirred at room temperature for 30 minutes. To the reaction mixture was then added, at room temperature, sodium triacetoxyborohydride (0.034 g, 0.16 mmol) under nitrogen atmosphere and the reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was then partitioned with aqueous NaHCO3 and dichloromethane. The organic layer was washed with brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield a crude oil. The crude oil was purified via flash chromatography (2.5% methanol/dichloromethane) to yield the title compound as a solid.

Provenance & Evidence