Diisobutylaluminum hydride → Tert-butyl 3-(hydroxymethyl)-4-methylpiperidine-1-carboxylate

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Reaction Steps

DIBAL-H (1 M in toluene, 27.3 mL, 27.3 mmol) was added drop-wise to a solution of 1-tert-butyl 3-methyl 4-methylpiperidine-1,3-dicarboxylate (3.35 g, 13.02 mmol, prepared using R from Preparation #Y.1 and P) in THF (40 mL) at about 0° C. The reaction mixture was stirred for about 1 h before quenching with 10% aqueous potassium sodium tartrate solution in water (50 mL). The reaction mixture was allowed to stir for about 1 h before it was concentrated under reduced pressure. The residue was partitioned with EtOAc (200 mL) and brine (3×100 mL). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated to constant weight to afford tert-butyl 3-(hydroxymethyl)-4-methylpiperidine-1-carboxylate as a clear oil (2.58 g, 86%): LC/MS (Table 2, Method a) Rt=2.10 min; MS m/z: 230 (M+H)+.

Provenance & Evidence