Benzaldehyde → (S)-2-benzylamino-3-phenyl-1-propanol
Reaction equation
[NH2:1][C@H:2]([CH2:10][OH:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H][H]>C(O)C.[Pt]>[CH2:12]([NH:1][C@H:2]([CH2:10][OH:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 600 °C
Procedure
L-Phenylalaninol (5 g, 33 mmoles) and 3.59 g (33.83 mmoles) of benzaldehyde were dissolved in 55 mL of 3A ethanol under inert atmosphere in a Parr shaker and the mixture was warmed to 600° C. for 2.7 hours. The mixture was cooled to approximately 250° C. and 0.99 g of 5% platinum on carbon was added and the mixture was hydrogenated at 60 psi of hydrogen and 400° C. for 10 hours. The catalyst was filtered off, the product was concentrated under reduced pressure and the crude solid product was recrystallized from 150 mL of heptane to give 3.83 g(48% yield) of N-benzyl-L-phenylalaninol as a white solid.
Workup
- temperatureThe mixture was cooled to approximately 250° C.
- filtrationThe catalyst was filtered off
- concentrationthe product was concentrated under reduced pressure
- customthe crude solid product was recrystallized from 150 mL of heptane
Sources & evidence
- ORD record
- ord-2fc63454b13a40fb8e3de4365d782d55
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06586627B1
Reaction notes
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