HCID 12045576, compound → HCID 70029841, compound

Participants

Reaction Steps

Borane-methyl sulfide complex (2.0M in tetrahydrofuran; 5.9 mL, 11.8 mmol) was added to a solution of the ethyl ester of trans-7-chloro-5-(2,3-ethylenedioxyphenyl)-1-neopentyl-1,2,3,5-tetrahydro-2-oxo-4,1-benzoxazepine-3-acetic acid (1.44 g, 2.95 mmol; Example 1D) in tetrahydrofuran (4.4 mL) under a nitrogen atmosphere. The reaction was stirred at ambient temperature for 18 hours and then cooled to 0° C. and quenched by slow addition of methanol. Once gas evolution ceased, an additional amount of methanol was added and the resulting mixture stirred 1 hour. The reaction mixture was then concentrated and the resulting residue taken up in water and extracted with ethyl acetate (3×). 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 (3:1 hexanes/ethyl acetae) to give 835 mg (66%) of the title compound as a white solid.

Provenance & Evidence