Acetic Acid → [3-(3-Phenylpropoxy)phenyl]methanol

HRID 275836Notes

Reaction equation

HRID 275836 reaction equation
N[C:2]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:20][C:3]=1[CH:4]([OH:19])C1C=CC=C(NC(OC(C)(C)C)=O)C=1.C(OC1C=CC(C=O)=CC=1)C1C=CC=CC=1.C(O)(=O)C.[BH4-].C([Na])#N>CO>[C:28]1([CH2:27][CH2:26][CH2:25][O:24][C:21]2[CH:22]=[CH:23][CH:2]=[C:3]([CH:20]=2)[CH2:4][OH:19])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 78109Benzaldehyde, 4-(phenylmethoxy)-HCID 538250882-Amino-alpha-(3-tert-butoxycarbonylaminophenyl)-5-(3-phenylpropyloxy)benzyl alcoholHCID 178511851HCID 178511851, compound

Product 1

HCID 28562026[3-(3-Phenylpropoxy)phenyl]methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

In methanol (12 ml) were dissolved 2-amino-α-(3-tert-butoxycarbonylaminophenyl)-5-(3-phenylpropyloxy)benzyl alcohol (0.7 g), 4-benzyloxybenzaldehyde (0.38 g) and acetic acid (0.1 g). To the solution was added cyano sodium borohydride (0.11 g). The mixture was stirred for 30 minutes at 60° C. The reaction mixture was concentrated, to which were added ethyl acetate (50 ml) and water (100 ml). The organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off to leave 2-(4-benzyloxybenzyl)-α-3-tert-butoxycarbonylaminomethylphenyl)-5-(3-phenylpropyloxy)benzyl alcohol as a yellow oily product (0.95 g).

Workup

  1. concentrationThe reaction mixture was concentrated, to which
  2. additionwere added ethyl acetate (50 ml) and water (100 ml)
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-37aebf7595b144f6b86e41da4ccc7802
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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