Ammonium formate → HCID 10176280, compound

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Reaction Steps

To a solution (70 mL) of lithium aluminum hydride (1.50 g, 39.5 mmol, 3.0 equivalents) in tetrahydrofuran was added dropwise a solution of (R)-N-(benzoyloxy-carbonyl)-3-amino-4-phenylbutanoic acid (4.84 g, 13.1 mmol), which was obtained by the method described in Tetrahedron, 44, p. 5525, 1988 and Journal of Organic Chemistry (J. Org. Chem.), 64, p. 6411, 1999, in tetrahydrofuran (30 mL) under ice cooling, and the mixture was stirred at room temperature for 30 minutes. After the reaction solution was cooled on ice, excess lithium aluminum hydride was decomposed with ethyl acetate and water. The deposited solid was removed by filtration using a filtration aid, and the filtrate was extracted with chloroform. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated. After the resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=50:50), the resulting (R)-N-(benzyloxycarbonyl)-3-amino-4-phenyl-1-butanol (1.37 g, 5.09 mmol) was dissolved in methanol (30 mL), and to the solution were added 20% palladium hydroxide/carbon (200 mg) and ammonium formate (1.30 g, 20.6 mmol, 4.1 equivalents), and then the mixture was stirred for 1 hour with heating. After the catalyst was removed by using a filtration aid, the solvent was evaporated. To the residue was added ethyl acetate, and the deposited solid was collected by filtration to obtain the title compound (730 mg, 87%).

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