Aluminium lithium hydride → HCID 21193307, compound

Participants

Reaction Steps

To a suspension of lithium aluminum hydride (0.32 g, 8.4 L s mmol) in anhydrous ether (50 ml) was added a solution of 4-(2-methylbenzyl) N-t-butoxycarbonyl isonipecotic acid benzyl ester (3.0 g, 7.1 mmol) in anhydrous ether (25 ml) over 15 min. The resulting mixture was heated gently at reflux for 1 h. The reaction mixture was then quenched with the slow and successive addition of H2O (0.32 ml), 15% aqueous NaOH, and H2O (0.96 ml). After sirring for 30 min., the mixture was filtered through Celite and the filtrate washed with brine, dried (MgSO4), and concentrated in vacuo to a colorless syrup. Purification by column chromatography on silica with 25%-50% EtOAc/hexane as eluent afforded the product as a colorless gum. This material was recrystallized from EtOAc and hexane to afford a white solid. m.p. 104°-106° C.

Provenance & Evidence