2-Methyl-2-butene → HCID 69558982, compound

Participants

Reaction Steps

To a stirred solution of 6-(3-pyrrolidin-1-yl-propoxy)-7-methoxy-1-(3-ethoxy-benzoyl)-isoquinoline-4-carbaldehyde (63 mg, 0.13 mmol) in t-butanol (0.5 mL) and water (0.5 mL) solution was added sodium dihydrogenphosphate monohydrate (73 mg, 0.53 mmol), 2-methyl-2-butene (0.089 mL, 0.80 mmol) and sodium chlorite (71.2 mg, 0.80 mmol) at room temperature. The reaction suspension was then stirred at room temperature for 14 hrs. The resulting two-phase mixture was partitioned between dichloromethane and water and acidified to pH=3 by addition of 1N hydrochloric acid. The aqueous phase was then extracted with dichloromethane (3×20 mL). The combined extracts were washed with saturated sodium chloride solution (30 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford a brown semi-solid oil. The crude product was recrystallized in ethyl acetate to afford 6-(3-pyrrolidin-1-yl-propoxy)-1-(3-ethoxy-benzoyl)-7-methoxy-isoquinoline-4-carboxylic acid hydrochloride (20 mg, 32% yield) as a light brown solid. HR-MS m/e calcd for C27H30N2O6 (M−H+) 479.2177, found 479.2182; 1H NMR (300 MHz) compatible.

Provenance & Evidence