Tetrahydrofuran → HCID 58635239, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-pyridylcarbinol (209 □L, 2.17 mmol) and dry THF (10 mL) at 0° C. under an atmosphere of nitrogen was added NaH (60% dispersion in mineral oil, 87 mg, 2.17 mmol), and the reaction mixture was stirred at 0° C. for 30 mins. This mixture was then added dropwise to a solution of (S)-1-(chlorocarbonyl)-2-piperidinecarboxylic acid methyl ester (EP 75737) (425 mg, 2.06 mmol) and dry THF (10 mL) at 0° C. The reaction mixture was allowed to stir for 1.5 h while warming to room temperature, then poured onto aq.KHSO3 (25 mL ) and extracted with EtOAc (2×50 mL). The combined organic phases were washed with aq.NaHCO3, followed by brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (30% ethyl acetate in hexane) to give the title compound as a colorless oil (340 mg, 59%): 1H NMR (400 MHz, CDCl3) δ 1.3–1.8 (5H, m), 2.3 (1H, bs), 3.0 (0.5H, t, J 12.0 Hz), 3.1 (0.5H, t, J 12.0 Hz), 3.9 (3H, s), 4.2 (1H, m), 5.0 (1H, m), 5.3 (2H, dd, J 14.0 Hz), 7.2–7.4 (2H, m), 7.7 (1H, m), 8.6 (1H, m)

Provenance & Evidence