2-Methyl-5-phenylisoxazolidine → 3-Methylamino-1-phenylpropanol

HRID 1417062Notes

Reaction equation

HRID 1417062 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:3]1>CCO.[Pd]>[CH3:1][NH:2][CH2:6][CH2:5][CH:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[OH:3]

Participants

4

Reactant 1

HCID 110519812-Methyl-5-phenylisoxazolidine

Product 1

HCID 27339893-Methylamino-1-phenylpropanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Methyl-5-phenylisoxazolidine (54.3 g, 333 mmol) and Pd/C (2.7 g) in EtOH (55.0 g) are heated to 60-80° C. in a 300-mL, stirred (700 rpm), Hastalloy autoclave which is kept pressurized to 55 psig with H2 for 5 hours. After cooling, the mixture is filtered and the EtOH removed in vacuo to give N-methyl-3-phenyl-3-hydroxypropylamine.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture is filtered
  3. customthe EtOH removed in vacuo

Sources & evidence

ORD record
ord-49d667579e5b4d4ba7baad4b02d1f2dd
Source dataset
uspto-grants-1999_06
Patent number
US05917091

Reaction notes

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