Pyridine → HCID 86758887, compound

Participants

Reaction Steps

Dess-Martin periodinane (979 mg, 2.31 mmol) was added to a solution of 2-[trans-7-chloro-5-(2,3-ethylenedioxyphenyl)-1-neopentyl-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]-ethanol (830 mg, 1.92 mmol), pyridine (980 mL) and methylene chloride (18 mL) at 0° C. The mixture was warmed to ambient temperature and stirred 40 minutes before adding more Dess-Martin periodinane (800 mg, 1.89 mmol). After an additional 15 minutes, the reaction was quenched by addition of 5:1 saturated aqueous sodium bicarbonate/saturated aqueous sodium sulfite, stirred 5 minutes, and extracted with ether (2×). The combined organics were washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and purified by flash column chromatography (9:1 hexanes/ethyl acetate) to give 562 mg (68%) of the title compound as a white foam.

Provenance & Evidence