Ethyl chloroformate → Tert-butyl 4-(hydroxymethyl)-4-phenylpiperidine-1-carboxylate

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Reaction Steps

1-(tert-Butoxycarbonyl)-4-phenylpiperidine-4-carboxylic acid (Bionet Co., 1.0 g) was dissolved in tetrahydrofuran (10 ml) and triethylamine (0.55 ml), and the mixture was cooled to 0° C. Under ice-cooling, ethyl chloroformate (0.34 ml) was added to the mixture, and the mixture was stirred for 30 min. Sodium borohydride (250 mg) was added and the mixture was stirred for 30 min. The mixture was warmed to room temperature and stirred for 2 hr. After completion of the reaction, 1N sodium hydroxide was added, and the mixture was extracted with ethyl acetate. The organic layer was dried and the solvent was evaporated under reduced pressure to give 4-(hydroxymethyl)-4-phenyl-1-piperidinecarboxylic acid tert-butyl ester (1.0 g, yield 98%).

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