Ammonia → Benzyl 4-hydrazinylpiperidine-1-carboxylate

Participants

Reaction Steps

A solution of 1-CBZ-4-piperidone (2.92 g, 12.5 mmol) and hydrazine hydrate (2.01 mL, 18.8 mmol) in MeOH (25 mL) was stirred at 50° C. for 30 min, then cooled to RT and NaBH4 (1.18 g, 31.3 mmol) added (CARE: gas evolution and exotherm to ˜45° C.). The solution was stirred at RT for 30 min, then 50° C. for 18 h. The cooled solution was concentrated in vacuo, suspended in water (25 mL) and extracted with DCM (2×25 mL). The combined organics were passed through a hydrophobic frit and concentrated in vacuo to leave a clear oil. FCC, using 0-10% [2H NH3 in MeOH] in DCM, gave the title compound as a clear oil (1.80 g, 58%). LCMS (Method 3): Rt 2.03 min, m/z 250 [MH+].

Provenance & Evidence