Triethylamine → HCID 178454074, compound

Participants

Reaction Steps

A solution of trans (4-tert-butoxycarbonylamino-cyclohexyloxy)-acetic acid (600 mg, 2.20 mmol) and triethylamine (400 μL, 2.90 mmol) in THF (22 mL) at 0° C. was treated dropwise with ethyl chloroformate (250 μL, 2.60 mmol). After 30 minutes ammonium hydroxide (2.20 mL, 170 mmol) was added dropwise. The golden solution was stirred at ambient temperature for 30 minutes and then concentrated under vacuum. The residue was partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate (2×). The combined organic extracts were washed with 1M HCl, a saturated sodium bicarbonate solution and brine, dried over sodium sulfate and concentrated under vacuum to afford 550 mg (92%) of trans (4-carbamoylmethoxy-cyclohexyl)-carbamic acid tert-butyl ester as a white solid. LCMS (Method Q, ESI): RT=2.82 min, m+H=295.0; 1H NMR (400 MHz, CDCl3) δ: 6.52 (s, 1H), 5.55 (s, 1H), 4.38 (s, 1H), 3.96 (s, 2H), 3.44 (s, 1H), 3.30 (m, 1H), 2.03 (d, 4H), 1.44 (s, 9H), 1.38 (m, 2H), 1.16 (m, 2H).

Provenance & Evidence