1-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid → Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

Participants

Reaction Steps

A solution of 25.03 g (109.2 mmole) N-Boc isonipecotic acid was dissolved in 200 mL TBF and treated with 200 mL 1 M borane-tetrahydrofuran complex in THF, and the mixture was stirred overnight. The mixture was concentrated under vacuum, diluted with 750 mL ethyl acetate, and washed with 150 mL 1 N HCl (6×) and then saturated brine. The organic layer was dried over sodium sulfate and concentrated to give 24.327 g of crude product as a white solid. H NMR (500 MHz) δ 4.15 (br d, J=13.7 Hz, 2H), 3.52 (d, J=6.2 Hz, 2H), 2.69-2.75 (m, 2H), 1.71-1.75 (m, 2H), 1.62-1.70 (m, 1H), 1.47 (s, 9H), 1.12-1.21 (m, 2H). This was used as is in the next step.

Provenance & Evidence