Acetic Acid → 4-((2S)-3-Amino-2-hydroxy-propoxy)-phenol

HRID 2188270Notes

Reaction equation

HRID 2188270 reaction equation
[NH2:1][CH2:2][C@H:3]([OH:20])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12]CC2C=CC=CC=2)=[CH:8][CH:7]=1.C(O)(=O)C.[H][H]>[Pd].C(O)C>[NH2:1][CH2:2][C@H:3]([OH:20])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 12044729(2S)-1-amino-3-(4-benzyloxy-phenoxy)-propan-2-ol2×HCID 178418361HCID 178418361, compound

Product 1

HCID 98775474-((2S)-3-Amino-2-hydroxy-propoxy)-phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (2S)-1-amino-3-(4-benzyloxy-phenoxy)-propan-2-ol (which was obtained in Intermediate 4) (0.9 g, 3.3 mmol), 0.2 mL of acetic acid and 10% palladium on carbon (0.3 g) in 70 mL of ethanol was pressurized with 20 psi hydrogen and shaken over 2 hours. The catalyst was then removed by filtering through a short pad of silica gel and the solvent was removed to give the title compound as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ1.86 (s, 1 H), 2.66 (dd, J=12.8, 5.3 Hz, 1H), 2.85 (dd, J=12.8, 3.5 Hz, 1H), 3.79-3.95 (m, 3 H), 6.67 (d, J=6.6 Hz, 2H), 6.75 (d, J=6.6 Hz, 2 H); MS (ES) m/z: 183.1 (MH+); HRMS Calcd. for C9H13NO3(MH+): 183.0895. Found: 183.0892.

Workup

  1. customThe catalyst was then removed
  2. filtrationby filtering through a short pad of silica gel
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-13b128e8ad944881b2895265d9c07d8d
Source dataset
uspto-grants-2002_06
Patent number
US06410734B1

Reaction notes

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