Methanol → 2-Amino-5-chloro-alpha-(4-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol

HRID 275850Notes

Reaction equation

HRID 275850 reaction equation
CO.[NH2:3][C:4]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:5]=1[C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:10][CH:9]=1)=[O:7].[BH4-].[Na+]>C(OC(=O)C)C>[NH2:3][C:4]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:5]=1[CH:6]([OH:7])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 183153642-Amino-4'-tert-butoxycarbonylaminomethyl-5-chlorobenzophenone

Product 1

HCID 545021332-Amino-5-chloro-alpha-(4-tert-butoxycarbonylaminomethylphenyl)benzyl alcoholYield 93.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a methanol (10 ml) solution of 2-amino-4′-tert-butoxycarbonylaminomethyl-5-chlorobenzophenone (0.9 g) was added sodium borohydride (0.28 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 dried over anhydrous Na2SO4. The solvent was then distilled off, and the residue was purified by means of a silica gel column chromatography to give the object 2-amino-5-chloro-α-(4-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.85 g) as a colorless oily product.

Workup

  1. washThe mixture was washed with water
  2. dry with materialdried over anhydrous Na2SO4
  3. distillationThe solvent was then distilled off
  4. customthe residue was purified by means of a silica gel column chromatography

Sources & evidence

ORD record
ord-4da33944a177480fbea22546decfe0d8
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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