Water → HCID 70663158, compound

Participants

Reaction Steps

To a suspension of 1-benzhydryl-3-(2-bromo-4-(diethoxymethyl)phenyl)-azetidine-3-carbonitrile (Preparation 16, 13.5 g, 26.7 mmol) in EtOH (150 mL) was added aq NaOH (85 mL of a 25% wt. solution). The reaction mixture was heated to reflux for 36 hours. Contents were concentrated under vacuum to remove EtOH to a concentration of ˜100 mL and solution became cloudy. The residue was placed in an ice bath and cooled. The pH of the residue was lowered to ˜5-7 by the slow addition of 3M HCl at which time a precipitate formed. Additional water was added and the mixture was stirred for 15 minutes and filtered. The precipitate was re-dissolved in EtOAc (250 mL) and washed with saturated NH4Cl and brine.

Provenance & Evidence