Water → (2R,5R)-5-[(1S,2S)-2-Amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2-(2,2-dimethylpropoxy)-morpholine-4-carboxylic acid tert-butyl ester

HRID 20409Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 20409
[BH4-].[Na+].[C:3]([O:7][C:8]([N:10]1[C@@H:15]([C@@H:16]([OH:30])[C@@H:17]([N+:27]([O-])=O)[CH2:18][C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=2)[CH2:14][O:13][C@@H:12]([O:31][CH2:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].O>CO.[Ni](Cl)Cl>[C:3]([O:7][C:8]([N:10]1[C@@H:15]([C@@H:16]([OH:30])[C@@H:17]([NH2:27])[CH2:18][C:19]2[CH:20]=[C:21]([F:26])[CH:22]=[C:23]([F:25])[CH:24]=2)[CH2:14][O:13][C@@H:12]([O:31][CH2:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:11]1)=[O:9])([CH3:4])([CH3:6])[CH3:5]

Komponenten

6

Edukt 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 68561911HCID 68561911, Verbindung

Produkt 1

HCID 68560376(2R,5R)-5-[(1S,2S)-2-Amino-3-(3,5-difluorophenyl)-1-hydroxypropyl]-2-(2,2-dimethylpropoxy)-morpholine-4-carboxylic acid tert-butyl esterAusbeute 78,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24385Nickel DichlorideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

Add sodium borohydride (0.86 g, 22.60 mmol) to (2R,5R)-5-[(1R,2S)-3-(3,5-difluorophenyl)-1-hydroxy-2-nitropropyl]-2-(2,2-dimethylpropoxy)-morpholine-4-carboxylic acid tert-butyl ester (2.30 g, 4.71 mmol) and nickel (II) chloride (1.34 g, 10.36 mmol) in methanol (47 mL) at room temperature over 2 minutes. Stir for 20 minutes, add water (˜3 mL) and concentrate. Dilute with ethyl acetate (˜75 mL), filter through Celite®, wash with 10% aqueous potassium carbonate, saturated aqueous sodium chloride, Dry (magnesium sulfate), filter and concentrate to give the title compound as an off-white solid (1.7 g, 78.7%).

Aufarbeitung

  1. concentrationconcentrate
  2. additionDilute with ethyl acetate (˜75 mL)
  3. filtrationfilter through Celite®
  4. washwash with 10% aqueous potassium carbonate, saturated aqueous sodium chloride
  5. dry with materialDry (magnesium sulfate)
  6. filtrationfilter
  7. concentrationconcentrate

Quellen und Nachweise

ORD-Eintrag
ord-8b398869883f4cee9a665ae17f210000
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745438B2

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