1,1-Dimethylethyl (3R,4R)-4-azido-3-hydroxy-1-piperidinecarboxylate → rac-tert-butyl (3R,4R)-4-amino-3-hydroxypiperidine-1-carboxylate

Participants

Reaction Steps

To a stirred solution of (±)-trans-4-azido-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (10 mmol, 2.42 g) in methanol (25 mL) was added 10% palladium on carbon (0.5 g, wet), and the resultant reaction mixture was subjected to hydrogenation using a balloon full of hydrogen for 8 h. The catalyst was filtered through a pad of celite, and the pad was with methanol (25 mL). The combined filtrate was concentrated under reduced pressure to provide (±)-trans-4-amino-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester.

Provenance & Evidence