Ethanol → 3-Methylamino-1-phenylpropanol
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.C(O)C>C1S(=O)(=O)CCC1.[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
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
2-Methyl-5-phenylisoxazolidine (38.1 g, 234 mmol) dissolved in tetramethylene sulfone (38.1 g) is mixed with 5% Pd/C (1.9 g) in a glass pressure reactor. The reactor is warmed to 50° C. and the pressure is maintained at 40 psig with H2 for 24 hours. Ethanol (38.1 g) is added and heating is continued for 48 hours. After cooling, the mixture is filtered and the EtOH is removed to give a solution of N-methyl-3-phenyl-3-hydroxypropylamine in tetramethylene sulfone.
Workup
- temperaturethe pressure is maintained at 40 psig with H2 for 24 hours
- temperatureheating
- temperatureAfter cooling
- filtrationthe mixture is filtered
- customthe EtOH is removed
Sources & evidence
- ORD record
- ord-a74ade672e0c4b3f9e2735af20885959
- Source dataset
- uspto-grants-1999_12
- Patent number
- US05998627
Reaction notes
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