Ammonium Chloride → HCID 66759199, compound

Participants

Reaction Steps

To a stirred solution of tert-butyl 4-{[(5-{2,4-bis[(2-methoxyethoxy)methoxy]-6-(4-nitrophenoxy)phenyl}isoxazol-3-yl)carbonyl]amino}piperidine-1-carboxylate (5.3 g, 7.4 mmol) in a mixture of dioxane (100 mL) and water (20 mL) were added portion wise zinc powder (1 g, 14.8 mmol, 2 eq.) and ammonium chloride (3.9 g, 74 mmol, 10 eq.) at 100° C. After stirring for 30 minutes, the reaction mixture was cooled and diluted with ethyl acetate. After washing with 1 M Na2CO3 solution, the organic phase was dried over Na2SO4 and the solvent removed. The crude product was filtered over a small pad of silica gel eluting with hexane/ethyl acetate 3/1 to provide the title compound (4.38 g, 86% yield).

Provenance & Evidence