Benzaldehyde → (S)-2-benzylamino-3-phenyl-1-propanol

HRID 11241

Reaction equation

HRID 11241 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]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 447213phenylalaninol, (S)-HCID 178418361HCID 178418361, compound

Product 1

HCID 10514267(S)-2-benzylamino-3-phenyl-1-propanolYield 48.1%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °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 60° C. for 2.7 hours. The mixture was cooled to approximately 25° C. and 0.99 g of 5% platinum on carbon was added and the mixture was hydrogenated at 60 psi of hydrogen and 40° 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

  1. temperatureThe mixture was cooled to approximately 25° C.
  2. filtrationThe catalyst was filtered off
  3. concentrationthe product was concentrated under reduced pressure
  4. customthe crude solid product was recrystallized from 150 mL of heptane

Sources & evidence

ORD record
ord-44a383223fe44b849e78edd1e0e8a2be
Source dataset
uspto-grants-2006_08
Patent number
US07098202B2

Linked notes

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