Tetrahydrofuran → HCID 86689152, compound

Participants

Reaction Steps

To a solution of (R)-3-amino-3-(6-bromo-3-fluoro-pyridin-2-yl)-2,2-difluoro-5-methoxy-pentan-1-ol (1.15 g, 3.35 mmol) in THF (27.9 ml) was added nitrobenzoyl-isothiocyanate (767 mg, 3.69 mmol). After stirring at rt for 4 hr DCC (760 mg, 3.69 mmol) and triethylamine (34.1 mg, 0.337 mmol) was added. Stirring was continued at rt for 19 hr and finally, the reaction mixture was kept at 70° C. for 5 h. The yellow-orange solution was cooled and evaporated in vacuo. The crude product (2.7 g) was chromatographed over silica gel (Redisep column 120 g, cyclohexane/ethyl acetate 7:3) to give the title compound as a light yellow foam. 650 mg (35.6% yield).

Provenance & Evidence