Methanol → HCID 16206167, compound

Participants

Reaction Steps

Ethyl 1-methyl-4-phenylpiperidine-4-carboxylate (2.7 g, 10 mmol) was dissolved in dry toluene (30 ml). The stirred solution was cooled to -63° C. under an atmosphere of N2, whereafter a solution of diisobutylaluminiumhydrid (DIBAH, 1 M, 20 ml) was added dropwise. Stirring was continued at -70° C. for 11/2 h, whereafter methanol (5 ml) was added, in order to destroy excess of DIBAH. At ambient temperature water (50 ml) was added, and the mixture was filtered through a pad of filter aid. The organic phase was dried over Na2SO4 and evaporated to leave an oily residue. Treatment with ether afforded precipitation of the side product 4-hydroxymethyl-1-methyl-4-phenylpiperidine as pale crystals. Filtration followed by evaporation of the filtrate left the title compound as an oil, which was processed without further purification.

Provenance & Evidence