Реакция #48660

ord-62b36ed08b1e48609c2690652dd529e3

Уравнение реакции

[H][H]
hydrogen
CC(C)(C)OC(=O)N1C[C@H](COC2CCCCC2)OC[C@@H]1[C@@H](OCc1ccccc1)[C@H](Cc1cc(F)cc(F)c1)N(Cc1ccccc1)Cc1ccccc1
(2R,5R)-5-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-2-cyclohexyloxymethyl-morpholine-4-carboxylic acid tert-butyl ester
→
CC(C)(C)OC(=O)N1C[C@H](COC2CCCCC2)OC[C@@H]1[C@@H](O)[C@@H](N)Cc1cc(F)cc(F)c1
desired compound
Выход 97.1%
CC(C)(C)OC(=O)N1C[C@H](COC2CCCCC2)OC[C@@H]1[C@@H](O)[C@@H](N)Cc1cc(F)cc(F)c1
(2R,5R)-5-[(1S,2S)-2-Amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2-cyclohexyloxymethylmorpholine-4-carboxylic acid tert-butyl ester
Выход 97.1%

Реактанты

[H][H]
hydrogen
CC(C)(C)OC(=O)N1C[C@H](COC2CCCCC2)OC[C@@H]1[C@@H](OCc1ccccc1)[C@H](Cc1cc(F)cc(F)c1)N(Cc1ccccc1)Cc1ccccc1
(2R,5R)-5-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-2-cyclohexyloxymethyl-morpholine-4-carboxylic acid tert-butyl ester

Реагенты

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

Растворители

CCO
ethanol

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ФильтрацияFilter through a filtering agent
  2. 2
    Промывкаwash with ethanol
  3. 3
    Концентрированиеconcentrate

Методика

Add 20% palladium hydroxide on carbon (0.772 g) to a solution of (2R,5R)-5-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-2-cyclohexyloxymethyl-morpholine-4-carboxylic acid tert-butyl ester (0.772 g, 1.023 mmol) in ethanol (10.2 mL). Stir vigorously under 1 atmosphere of hydrogen gas for 60 hours. Filter through a filtering agent, wash with ethanol and concentrate to give the desired compound (0.481 g, 97.1%).

Источник

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