Acetic Acid → HCID 67602990, compound

Participants

Reaction Conditions

Reaction Steps

a') A solution of 3-methoxy-1-(phenylmethyl)-4-piperidinone (4.4 g) in tetrahydrofuran was cooled to -75° C. Lithium tris-sec-butylborohydride was added dropwise and the reaction mixture was stirred for 2 hours at -70° C. Acetic acid 10% (100 ml) was added dropwise at room temperature. The organic solvent was evaporated. The aqueous residue was alkalized with NH4OH, then extracted twice with diisopropylether. The separated organic layer was washed with water, dried over MgSO4, filtered and the solvent was evaporated. The residue was purified by short column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 95/5 upgrading to 98/2), yielding 1.3 g (29.4%) of cis-3-methoxy-1-(phenylmethyl)-4-piperidinol (intermediate 2).

Provenance & Evidence