(2S,3S,5R)-5-[(1S,2S)-1-Benzyloxy-3-(3-benzyloxy-5-fluoro-phenyl)-2-dibenzylaminopropyl]-3-methyl-2-(2,2,2-trifluoro-ethoxy)-morpholine-4-carboxylic acid tert-butyl ester → (2S,3S,5R)-5-[(1S,2S)-2-Amino-3-(3-fluoro-5-hydroxy-phenyl)-1-hydroxy-propyl]-3-methyl-2-(2,2,2-trifluoro-ethoxy)-morpholine-4-carboxylic acid tert-butyl ester

Participants

Reaction Steps

Add 20% palladium hydroxide on carbon (200 mg) to a solution of (2S,3S,5R)-5-[(1S,2S)-1-benzyloxy-3-(3-benzyloxy-5-fluoro-phenyl)-2-dibenzylamino-propyl]-3-methyl-2-(2,2,2-trifluoro-ethoxy)-morpholine-4-carboxylic acid tert-butyl ester (116 mg, 0.138 mmol) in tert-butanol (10 mL). Heat to 45° C. and hydrogenate at 50 psi hydrogen gas for 18 hours. Filter and evaporate to give the desired compound (77 mg). MS(ESI): m/z=483 [M+H]+.

Provenance & Evidence