(RS)-1,1-Dimethylethyl 4-(1,2-Dihydroxyethyl)-4-(phenylmethoxymethyl)-1-piperidinecarboxylate → Tert-butyl 4-(1,2-dihydroxyethyl)-4-(hydroxymethyl)piperidine-1-carboxylate

Participants

Reaction Steps

A slurry of palladium on carbon (10%, 100 mg) in ethanol (10 mL) was added to a solution of (RS)-1,1-dimethylethyl 4-(1,2-dihydroxyethyl)-4-(phenylmethoxymethyl)-1-piperidinecarboxylate (Description 97, 1.05 g, 2.9 mmol) in ethanol (30 mL) and the mixture was shaken under hydrogen (50 psi) for 72 hours. The mixture was filtered through Celite™ and the solvent was evaporated under reduced pressure to give the title compound as a pale oil (615 mg, 77%). m/z (ES+) 276 (M+1).

Provenance & Evidence