Ethyl chloroformate → 4-Piperidinol, 4-[2-(hydroxymethyl)phenyl]-1-methyl-

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Reaction Steps

A solution of 5.8 g. of 1'-benzyl-1,3-dihydrospiro[isobenzofuran-1,4'-piperidine]-3-one, 40 ml. of benzene, and 2.5 ml. of ethyl chloroformate is heated under reflux for 18 hours and concentrated to a solid. Recrystallization from benzene-cyclohexane provides colorless crystals, m.p. 150°-151°, of 1,3-dihydro-1'-ethoxycarbonylspiro[isobenzofuran-1,4'-piperidine]-3-one. Reduction with lithium aluminum hydride by the method described in Example 16b provides 4-hydroxy-4-(α-hydroxy2-tolyl)-1-methylpiperidine, m.p. 118°-119°.

Provenance & Evidence