Aluminium lithium hydride → HCID 10182411, compound

Participants

Reaction Conditions

Reaction Steps

A solution 6-[3-cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-propionylamino]-nicotinic acid methyl ester (prepared in Example 25B-a, 140 mg, 0.29 mmol) in diethyl ether (2 mL) was cooled to 0° C. and then slowly treated with lithium aluminum hydride powder (17 mg, 0.44 mmol). The reaction mixture was stirred at 0° C. for 30 min and then allowed to warm to 25° C. where it was stirred for 3.5 h. The reaction mixture was then slowly quenched by the dropwise addition of water (5 mL). The resulting mixture was partitioned between water (25 mL) and ethyl acetate (25 mL), and the layers were separated. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-N-(5-hydroxymethyl-pyridin-2-yl)-2-(4-naphthalen-1-yl-phenyl)-propionamide (47 mg, 37%) as a light yellow foam: mp 72-75° C.; EI-HRMS m/e calcd for C30H30N2O2 (M+) 450.2307, found 450.2312.

Provenance & Evidence