Sodium periodate → HCID 86682413, compound

Participants

Reaction Steps

To a solution of 8-[(1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl]-5-[(6-chloropyridin-3-yl)methyl]-9-(2,3-dihydroxypropyl)-8,9-dihydro-7H-pyrrolo[3,4-h]quinolin-7-one (Example 21, 0.050 g, 0.084 mmol) in a mixture of 0.8 mL of acetonitrile and 0.6 mL of water at 0° C. was added sodium periodate (0.018 g, 0.084 mmol). After 1.5 hr, the mixture was diluted with dichloromethane, filtered through Celite, and poured into saturated aqueous sodium bicarbonate. The mixture was extracted 3× with dichloromethane and the combined organic extracts were dried with sodium sulfate, filtered, and concentrated in vacuo to provide {8-[(1S,2S)-2-{[tert-butyl(dimethyl)silyl]oxy)cyclohexyl]-5-[(6-chloropyridin-3-yl)methyl]-7-oxo-8,9-dihydro-7H-pyrrolo[3,4-h]quinolin-9-yl}acetaldehyde that gave a mass ion (ES+) of 564.5 for [M+H]+.

Provenance & Evidence