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

HRID 1585839Notes

Reaction equation

HRID 1585839 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-92c33ac83ad441e99bf154f4d3494e42
Source dataset
uspto-grants-1999_08
Patent number
US05939587

Reaction notes

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