Borane;tetrahydrofuran → HCID 52913601, compound

Participants

Reaction Steps

To a stirred solution of acetic acid (5S,6S,7R,8S)-6,7-diacetoxy-5-[4-chloro-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-phenyl]-4-oxa-spiro[2.5]oct-8-yl ester (100 mg, 0.18 mmol) in THF (6 mL) was added a solution of BH3-THF (2.2 ml, 1.8 mmol) and heated to reflux overnight. Reaction was quenched with the addition of ethyl acetate. The solvent was evaporated and the crude product was purified by silica gel column chromatography to furnish the acetic acid (5S,6S,7R,8S)-6,7-diacetoxy-5-[4-chloro-3-(3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)-phenyl]-4-oxa-spiro[2.5]oct-8-yl ester (56 mg).

Provenance & Evidence