L-Phenylalanine → 3-Cyclohexyl-L-alanine

HRID 374688Notes

Reaction equation

HRID 374688 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H][H]>C(O)(=O)C.[Pt]=O>[CH2:7]1[CH2:6][CH2:5][CH:4]([CH2:3][C@H:2]([NH2:1])[C:10]([OH:12])=[O:11])[CH2:9][CH2:8]1

Participants

5

Reactant 2

HCID 6140L-PhenylalanineHCID 178418361HCID 178418361, compound

Product 1

HCID 7124213-Cyclohexyl-L-alanineYield 106.1%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

2 g of L-phenylalanine was dissolved in 30 ml of 50% acetic acid, and high pressure hydrogenation was conducted (hydrogen pressure: 50 kg/cm2, 40°-70° C., two hours) by an addition of 200 mg of platinum oxide. The catalyst was removed by filtration, and the solvent was distilled off under reduced pressure to obtain 2.2 g of L-cyclohexylalanine as colorless needles.

Workup

  1. customThe catalyst was removed by filtration
  2. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-583e9d4076574a6ca7ba14c4a7b8b7a9
Source dataset
uspto-grants-1996_01
Patent number
US05481036

Reaction notes

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