Aluminium lithium hydride → HCID 10202012, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 6-[3-cyclopentyl-2-(4-phenoxy-phenyl)-propionylamino]-nicotinic acid methyl ester (prepared in Example 30B-b, 59 mg, 0.13 mmol) in diethyl ether (5 mL) was cooled to 0° C. and then treated with lithium aluminum hydride (8 mg, 0.20 mmol). The reaction was slowly warmed to 25° C. where it was stirred for 16 h. At this time, the reaction mixture was slowly diluted with water (5 mL) and then extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50/50 hexanes/ethyl acetate) afforded 3-cyclopentyl-N-(5-hydroxymethyl-pyridin-2-yl)-2-(4-phenoxy-phenyl)-propionamide (28 mg, 51%) as a yellow foam: FAB-HRMS m/e calcd for C26H28N2O3 (M+H)+ 417.2178. found 417.2163.

Provenance & Evidence