Dichloromethane → HCID 86682407, compound

Participants

Reaction Steps

To a 15 mL dichloromethane solution of 5-bromo-8-[(1S,2S)-2-hydroxycyclohexyl]-3,9-dihydro-7H-pyrrolo[3,4-h]quinolin-7-one (2.00 g, 5.54 mmol) at 0° C. was added 2,6 lutidine (1.29 mL, 11.1 mmol) and tert-butyldimethylsilyl trifluoromethanesulfonate (1.91 mL, 8.30 mmol). The mixture was warmed to ambient temperature, and after 15 hr, diluted with water and extracted 2× with ethyl acetate. The combined organic extracts were washed with brine, dried with magnesium sulfate, filtered, and concentrated in vacuo. The resultant white crystals were collected via filtration and washed with hexanes to provide 5-bromo-8-[(1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl]-8,9-dihydro-7H-pyrrolo[3,4-h]quinolin-7-one that gave a proton NMR spectra consistent with theory.

Provenance & Evidence