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

HRID 962939Notes

Reaction equation

HRID 962939 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 (12.6 g, 77.3 mmol) in EtOH (134 g) is mixed with 5 Pd/C (1.2 g) in a glass pressure reactor. The reactor is warmed to 40°-50° C. and the pressure maintained at 40 psig with H2 until the pressure becomes constant (ca. 24 hours). The mixture is filtered through Celite and the solvent is removed to give N-methyl-3phenyl-3-hydroxypropylamine.

Workup

  1. temperatureThe reactor is warmed to 40°-50° C.
  2. temperaturethe pressure maintained at 40 psig with H2 until the pressure
  3. custom(ca. 24 hours)
  4. filtrationThe mixture is filtered through Celite
  5. customthe solvent is removed

Sources & evidence

ORD record
ord-c1d2839b083c47098ddc6c5fb6e419d7
Source dataset
uspto-grants-1998_06
Patent number
US05760243

Reaction notes

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