Triethylamine → HCID 21224336, compound

Participants

Reaction Conditions

Reaction Steps

Trifluoromethanesulfonic anhydride (2.60 mL, 15.39 mmol), followed by triethylamine (4.30 mL, 30.78 mmol) was added to a slurry of N-(tert-butoxycarbonyl)-4-hydroxymethylpiperidine-4-carboxylic acid (3.80 g, 14.65 mmol) in anhydrous diethyl ether (27 mL) cooled to 0° C. The biphasic solution was stirred for 23 hours, warmed to room temperature, stirred an addition 1 hour, and the upper diethyl ether layer separated by decantation. The lower was extracted with additional portions of diethyl ether (2×100 mL), and the combined organic extracts washed with aqueous sodium bicarbonate solution (2×50 mL), dried over magnesium sulfate, and concentrated in vacuo to afford 7-(butoxycarbonyl)-2-oxa-7-azaspiro[3.5]nonan-1-one as a pale yellow oil (2.88 g, 82%). 1HNMR (CDCl3) δ 1.48 (s, 9H), 1.79-1.89 (m, 2H), 2.02-2.10 (m, 2H), 3.48-3.66 (m, 4H), 4.13 (s, 2H).

Provenance & Evidence