Diisopropylamine → 2-(1-Benzyl-4-hydroxypiperidin-4-yl)acetic acid

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Reaction Steps

A mixture of 2.12 g diisopropylamine and 15 ml tetrahydrofuran is stirred under argon at 0°. To this solution is added over two minutes 14 ml of 1.5 M n-butyllithium. To this solution at 0° is added 0.6 g acetic acid. The mixture is stirred five minutes at 20° and then cooled to -70°. To this mixture is added a solution of 1.89 g N-benzyl-4-piperidone in 4 ml tetrahydrofuran. The mixture is allowed to warm to room temperature and poured into 50 ml 1% sodium hydroxide. This mixture is extracted with three 50 ml portions of diethyl ether. The aqueous phase is adjusted to pH 7.0 with 3 N hydrochloric acid and is extracted with five 40 ml portions of dichloromethane. Evaporation of the dichloromethane affords (1-benzyl-4-hydroxypiperidin-4-yl)acetic acid.

Provenance & Evidence