Water → HCID 18612673, compound

Participants

Reaction Steps

[Naphthalen-1-ylmethyl-(3-phenyl-isoxazol-5-yl)-amino]-acetic acid ethyl ester (305 mg, 0.789 mmol) was dissolved in tetrahydrofuran (THF, 2 ml) and while stirring under argon, treated with a 1.0M ithium aluminum hydride in di ethyl ether solution (1.58 ml, 1.58 mmol) and stirred at rt for 1.5 hr. The reaction was diluted with THF (2 ml), followed by diethyl ether (10 ml), and water was added slowly dropwise to give a filterable solid. The mixture was filtered through super cel, the filter cake washed well with a THF/diethyl ether (1/4), and the filtrate stripped to dryness in vacuo to give a crude oil (200 mg). Flash chromatography on silica gel (10 to 15% diethyl ether in methylene chloride) gave the product as a white foam (179 mg, 65.9%).

Provenance & Evidence