Water → HCID 123476531, compound

Participants

Reaction Steps

To a solution of 5-bromo-2-[(1S,2S)-2-hydroxycyclohexyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one (see Example 1, 2.00 g, 5.55 mmol) in 15 mL of dichloromethane at 0° C. was added 2,6-lutidine (1.29 mL, 11.1 mmol) and tert-butyldimethylsilyl trifluoromethanesulfonate (1.91 mL, 8.33 mmol). The mixture was warmed to ambient temperature and after 15 hr, was treated with water. The mixture was extracted 2× with ethyl acetate and the combined organic extracts were washed with brine, dried with magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-40% ethyl acetate in hexanes, to provide 5-bromo-2-[(1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one that gave a mass ion (ES+) of 475.1 for [M+H]+.

Provenance & Evidence