Sodium borohydride → 2-Amino-alpha-(3-tert-butoxycarbonylaminomethylphenyl)-5-isobutyloxybenzyl alcohol

HRID 275840Notes

Reaction equation

HRID 275840 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[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+]>CO>[NH2:1][C:2]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[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

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 183153652-Amino-3'-tert-butoxycarbonylaminomethyl-5-isobutyloxy-benzophenone

Product 1

HCID 542166762-Amino-alpha-(3-tert-butoxycarbonylaminomethylphenyl)-5-isobutyloxybenzyl alcohol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (12 ml) was dissolved 2-amino-3′-tert-butoxycarbonylaminomethyl-5-isobutyloxy-benzophenone (0.38 g). To the solution was added, while stirring at room temperature, sodium borohydride (50 mg). The reaction mixture was concentrated, to which was added water, followed by extraction with ethyl acetate (50 ml). The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off to leave 2-amino-α-(3-tert-butoxycarbonylaminomethylphenyl)-5-isobutyloxy-benzyl alcohol as a yellow oily product (0.36 g).

Workup

  1. additionTo the solution was added
  2. concentrationThe reaction mixture was concentrated, to which
  3. additionwas added water
  4. extractionfollowed by extraction with ethyl acetate (50 ml)
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-68faad7321444b02bb36d37ebf32d4d3
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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