Morpholine → HCID 59180433, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 74 (1.02 g; 2.7 mmol) in anhydrous toluene (13.3 mL) were added morpholine (0.28 mL; 3.2 mmol), sodium tert-butoxide (0.52 g; 5.4 mmol), bis(dibenzylideneacetone)palladium(0) (79 mg; 0.1 mmol), and racemic-BINAP (104 mg; 0.2 mmol), sequentially. Additional toluene (13.3 mL) was added to aid in stirring. The reaction mixture was put under nitrogen atmosphere (flush×3) and then heated at 100° C. for 16 hours. After cooling to room temperature, the reaction mixture was extracted with dichloromethane (70 mL) and washed with aqueous hydrochloric acid (30 mL×2; 2N), water (30 mL), and aqueous saturated sodium chloride (30 mL). The dichloromethane extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield a yellow gel. The crude product was purified by silica gel chromatography (16% to 25% to 33% to 66% ethyl acetate in hexanes to 10% methanol in dichloromethane gradient) to yield the title compound as a pale yellow solid (307 mg).

Provenance & Evidence