Triethylamine → HCID 86670527, compound

Participants

Reaction Steps

To a stirring dichloromethane (50 mL) solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (3.90 g, 19.4 mmol), 4-(dimethylamino)pyridine (0.23 g, 1.9 mmol), and triethylamine (8.0 mL, 57 mmol) was added 4-(trifluoromethyl)benzenesulfonyl chloride (4.75 g, 19.4 mmol). The reaction mixture was stirred for two hours at room temperature. The reaction was quenched with 1.0 M hydrochloric acid (100 mL) and extracted with diethyl ether (2×250 mL). The combined organic extracts were dried (magnesium sulfate), filtered and concentrated in vacuo to afford the crude product. It was used in the subsequent step without further purification. 1H NMR (500 MHz, CDCl3) δ 8.06 (d, J=8.2 Hz, 2H), 7.83 (d, J=8.2 Hz, 2H), 4.79 (tt, J=7.6, 3.6 Hz, 1H), 3.62 (ddd, J=13.6, 7.4, 4.0 Hz, 2H), 3.27 (ddd, J=13.8, 7.8, 3.9 Hz, 2H), 1.86-1.79 (m, 2H), 1.75-1.68 (m, 2H), 1.44 (s, 9H).

Provenance & Evidence