Methanol → 2-Amino-5-chloro-alpha-[4-(2-tert-butoxycarbonylaminoethyl)phenyl]benzyl alcohol

HRID 275853Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 275853
CO.[NH2:3][C:4]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:5]=1[C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:10][CH:9]=1)=[O:7].[BH4-].[Na+]>C(OC(=O)C)C>[NH2:3][C:4]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:5]=1[CH:6]([OH:7])[C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:18])=[CH:12][CH:13]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 183153782-Amino-4'-(2-tert-butoxycarbonylaminoethyl)-5-chlorobenzophenone

Produkt 1

HCID 696967742-Amino-5-chloro-alpha-[4-(2-tert-butoxycarbonylaminoethyl)phenyl]benzyl alcoholAusbeute 109,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a methanol (40 ml) solution of 2-amino-4′-(2-tert-butoxycarbonylaminoethyl)-5-chlorobenzophenone (2.0 g) was added sodium borohydride (0.5 g). The mixture was stirred for 30 minutes at room temperature, to which was added acetic acid ethyl ester (100 ml). The mixture was washed with water and, then, dried over anhydrous MgSO4, followed by distilling off the solvent. The residue was purified by means of a silica gel column chromatography to give the object 2-amino-5-chloro-α-[4-(2-tert-butoxycarbonylaminoethyl)phenyl]benzyl alcohol (2.2 g) as a colorless oily product.

Aufarbeitung

  1. washThe mixture was washed with water
  2. dry with materialdried over anhydrous MgSO4
  3. distillationby distilling off the solvent
  4. customThe residue was purified by means of a silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3adf72da0be14c7887c69b66cc2df0cc
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06352982B1

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