Реакция #48643

ord-a8675aa72d434460a404a5573ed3724f

Уравнение реакции

[H][H]
hydrogen
CC(C)(C)OC(=O)N1C[C@H](CCC2CCCCC2)OC[C@@H]1[C@@H](OCc1ccccc1)[C@H](Cc1cc(F)cc(F)c1)N(Cc1ccccc1)Cc1ccccc1
5-(R)-[1-(S)-benzyloxy-2-(S)-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-2-(S)-(2-cyclohexylethyl)-morpholine-4-carboxylic acid tert-butyl ester
→
CC(C)(C)OC(=O)N1C[C@H](CCC2CCCCC2)OC[C@@H]1[C@@H](O)[C@@H](N)Cc1cc(F)cc(F)c1
desired compound
CC(C)(C)OC(=O)N1C[C@H](CCC2CCCCC2)OC[C@@H]1[C@@H](O)[C@@H](N)Cc1cc(F)cc(F)c1
5-(R)-[2-(S)-Amino-3-(3,5-difluorophenyl)-1-(S)-hydroxypropyl]-2-(S)-(2-cyclohexylethyl)-morpholine-4-carboxylic acid tert-butyl ester

Реактанты

[H][H]
hydrogen
CC(C)(C)OC(=O)N1C[C@H](CCC2CCCCC2)OC[C@@H]1[C@@H](OCc1ccccc1)[C@H](Cc1cc(F)cc(F)c1)N(Cc1ccccc1)Cc1ccccc1
5-(R)-[1-(S)-benzyloxy-2-(S)-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-2-(S)-(2-cyclohexylethyl)-morpholine-4-carboxylic acid tert-butyl ester

Реагенты

[OH-].[OH-].[Pd+2]
palladium hydroxide on carbon

Растворители

CO
methanol

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Фильтрацияfilter through a pad of Celite®
  2. 2
    Концентрированиеconcentrate

Методика

Add 20% palladium hydroxide on carbon (Pearlman's catalyst) (232 mg) to a solution of 5-(R)-[1-(S)-benzyloxy-2-(S)-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-2-(S)-(2-cyclohexylethyl)-morpholine-4-carboxylic acid tert-butyl ester (232 mg, 0.31 mmol) in methanol (5 mL). Stir under 1 atmosphere of hydrogen gas at room temperature overnight, filter through a pad of Celite® and concentrate to give the desired compound as a colorless oil which is used directly without further purification (138 mg, 93%).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US07745438B2uspto-grants-2010_06