Methanol → 1-Benzyl 4-methyl piperidine-1,4-dicarboxylate

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Reaction Steps

SOCl2 (9.62 mL, 132 mmol, 2 eq.) was carefully added to cold MeOH (130 mL) at −30° C. followed by the addition of 1-benzyloxycarbonyl-piperidine-4-carboxylic acid (17.3 g, 66 mmol) in one portion. The mixture was stirred at room temperature for 3 h then was bubbled with N2 inside the hood and the resulting solution was concentrated by rotary evaporation. The residue was taken up into EtOAc (200 mL) and washed with saturated aqueous NaHCO3 (200 mL) and saturated brine (100 mL) and the organic extracts were dried over Na2SO4, filtered and concentrated by rotary evaporation to give 1-benzyloxycarbonyl-piperidine-4-carboxylic acid methyl ester as a colorless oil (15 g, 54 mmol, 82%). 1H NMR (300 MHz, CDCl3): δ 7.46 (m, 5H), 5.24 (s, 2H), 4.21 (m, 2H), 3.81 (s, 3H), 3.05 (t, 2H), 2.60 (m, 1H), 2.03 (m, 2H), 1.78 (m, 2H).

Provenance & Evidence