Ethyl Acetate → 2-Amino-5-chloro-alpha-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol

HRID 275829Notes

Reaction equation

HRID 275829 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:7]=1)=[O:5].[BH4-].[Na+].C(OC(=O)C)C>CO>[NH2:1][C:2]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:3]=1[CH:4]([OH:5])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][NH:13][C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15])[CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 183153602-Amino-3'-tert-butoxycarbonylaminomethyl-5-chlorobenzophenone

Product 1

HCID 543588652-Amino-5-chloro-alpha-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcoholYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-amino-3′-tert-butoxycarbonylaminomethyl-5-chlorobenzophenone (7 g) in methanol (70 ml) was added sodium borohydride (1.1 g), and the mixture was stirred for 30 minutes at room temperature. To the reaction mixture was added acetic acid ethyl ester (100 ml). The mixture was washed with water and 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-(3-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (6.9 g) as a colorless oily compound.

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-d91460066bc045f193de812fd0b65b43
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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