Triethylamine → HCID 58317738, compound

Participants

Reaction Steps

To a cooled mixture of Et3N (9.49 g, 94.0 mmol) and (1S,2S,4R)-2-azido-4-(benzyloxy)cyclopentanol (18.25 g, 78.3 mmol) in DCM (500 mL) was added dropwise methanesulfonyl chloride (9.87 g, 86.2 mmol) in DCM (50 mL) at 0° C. The mixture was stirred overnight at a temperature of 0° C. to RT. After complete conversion, aq NaHCO3 (5%, 300 mL) was added. The mixture was extracted with DCM, washed with brine, and dried over Na2SO4 to give the title compound as an oil (23.58 g, 75.8 mmol). 1H NMR (400 MHz, CDCl3) δ ppm 1.83-1.89 (m, 1 H), 2.06-2.13 (m, 1 H), 2.34-2.49 (m, 2 H), 3.04 (s, 3 H), 3.94-3.99 (m, 1 H), 4.08-4.13 (m, 1 H), 4.64 (s, 2 H), 4.93-4.98 (q, J=5.6/7.0 Hz, 1 H), 7.25-7.36 (m, 5 H).

Provenance & Evidence