1-[(Tert-butoxy)carbonyl]piperidine-2-carboxylic acid → N-Boc-piperidine-2-methanol

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Reaction Steps

Piperidine-1,2-dicarboxylic acid 1-tert-butyl ester (50 g, 218.1 mmol) in dry THF (300 mL) was cooled to −78° C. followed by adding BH3-THF solution (261.7 mL, 260.0 mmol) dropwise over 1 h. The resulting mixture was warmed to RT and stirred for 48 h. The reaction was quenched with HOAc/H2O (1:1 ratio, 100 mL). The resulting mixture was partitioned between EtOAc and sat. NaHCO3. The organic layer was washed with more sat. NaHCO3, H2O, brine, and dried over MgSO4. Concentration in vacuo gave a white solid. MS m/z: 216.2 (M+H). Calc'd. for C11H21NO3-215.15.

Provenance & Evidence