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

HRID 275853Notes

Reaction equation

HRID 275853 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 696967742-Amino-5-chloro-alpha-[4-(2-tert-butoxycarbonylaminoethyl)phenyl]benzyl alcoholYield 109.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3adf72da0be14c7887c69b66cc2df0cc
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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