Benzyl Alcohol → 4-Benzyl 1-tert-butyl piperidine-1,4-dicarboxylate

Participants

Reaction Steps

To a solution of N-t-butoxycarbonyl isonipecotic acid (12.0 g, 52.3 mmol) in 100 ml of anhydrous CH2Cl2, was added benzyl alcohol (6.0 ml, 58 mmol), followed by 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide hydrochloride (11.04 g, 57.6 mmol), and 4-dimethylaminopyridine (642 mg, 5.25 mmol). The resulting mixture was stirred for 6 hours then diluted with CH2Cl2 (150 ml) and washed successively with H2O, 10% aqueous citric acid, saturated NaHCO3, brine and then dried over MgSO4. Concentration in vacuo afforded a colorless oil which was chromatographed on silica with 20% EtOAc/hexane as eluent. Appropriate fractions were combined and concentrated in vacuo to afford the product as a white solid.

Provenance & Evidence