Reaktion #48621

ord-e09ff7f8a5644452bfc3792fcaa0c5db

Reaktionsgleichung

CCCC(=O)OC[C@H]1CN(C(=O)OC(C)(C)C)[C@@H]([C@@H](OCc2ccccc2)[C@H](Cc2cc(F)cc(F)c2)N(Cc2ccccc2)Cc2ccccc2)CO1
(2R,5R)-5-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-2-butyryloxymethyl-morpholine-4-carboxylic acid tert-butyl ester
[H][H]
hydrogen
→
CCCC(=O)OC[C@H]1CN(C(=O)OC(C)(C)C)[C@@H]([C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)CO1
desired compound
Ausbeute 100.2%
CCCC(=O)OC[C@H]1CN(C(=O)OC(C)(C)C)[C@@H]([C@@H](O)[C@@H](N)Cc2cc(F)cc(F)c2)CO1
(2R,5R)-5-[(1S,2S)-2-Amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2-butyryloxymethyl-morpholine-4-carboxylic acid tert-butyl ester
Ausbeute 100.2%

Edukte

CCCC(=O)OC[C@H]1CN(C(=O)OC(C)(C)C)[C@@H]([C@@H](OCc2ccccc2)[C@H](Cc2cc(F)cc(F)c2)N(Cc2ccccc2)Cc2ccccc2)CO1
(2R,5R)-5-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-2-butyryloxymethyl-morpholine-4-carboxylic acid tert-butyl ester
[H][H]
hydrogen

Reagenzien

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

Lösungsmittel

CCO
ethanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationFilter through a filtering agent
  2. 2
    Waschenwash with ethanol
  3. 3
    EinengenConcentrate the filtrate

Vorschrift

Dissolve (2R,5R)-5-[(1S,2S)-1-benzyloxy-2-dibenzylamino-3-(3,5-difluorophenyl)-propyl]-2-butyryloxymethyl-morpholine-4-carboxylic acid tert-butyl ester (295 mg, 0.397 mmol) in ethanol (29 mL). Add 20% palladium hydroxide on carbon (330 mg) and stir under 1 atmosphere of hydrogen gas for 48 hours. Filter through a filtering agent and wash with ethanol. Concentrate the filtrate to give the desired compound as a white foam (188 mg, 100%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07745438B2uspto-grants-2010_06