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

HRID 275844Notes

Reaction equation

HRID 275844 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][CH:11]=[CH:10][C:9]=1[CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[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][CH:11]=[CH:10][C:9]=1[CH2:14][NH:15][C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 183153772-Amino-2'-tert-butoxycarbonylaminomethyl-5-chlorobenzophenone

Product 1

HCID 539893822-Amino-5-chloro-alpha-(2-tert-butoxycarbonylaminomethylphenyl)benzyl alcoholYield 99.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a methanol (5 ml) solution of 2-amino-2′-tert-butoxycarbonylaminomethyl-5-chlorobenzophenone (0.5 g) was added sodium borohydride (79 mg). The mixture was stirred for 3 hours at room temperature. To the reaction mixture was added acetic acid ethyl ester (100 ml), which was washed with water and, then, dried over anhydrous MgSO4. The solvent was distilled off, and the residue was purified by means of a silica gel column chromatography to give the object 2-amino-5-chloro-α-(2-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.5 g) as a colorless oily product.

Workup

  1. washwas washed with water
  2. dry with materialdried over anhydrous MgSO4
  3. distillationThe solvent was distilled off
  4. customthe residue was purified by means of a silica gel column chromatography

Sources & evidence

ORD record
ord-fb242133f4ca4d78ba15ec50d239e3ba
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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