Pyridoxal 5'-phosphate → 1-Methyl-3-phenylpropylamine

HRID 1970760Notes

Reaction equation

HRID 1970760 reaction equation
[C:1]1([CH2:7][CH2:8][C:9](=O)[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC1[N:18]=CC(COP(O)(O)=O)=C(C=O)C=1O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O>[C:1]1([CH2:7][CH2:8][CH:9]([NH2:18])[CH3:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1051Pyridoxal 5'-phosphateHCID 17355Benzyl acetoneHCID 62657Potassium Phosphate, Tribasic

Product 1

HCID 311601-Methyl-3-phenylpropylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In the same manner as in Example 12, a cell-dispersion solution was prepared. Into a flask in which substrates, that is, 504.6 mg of 1-phenyl-3-butanone and 618.8 mg of (S)-α-phenethylamine were added in advance, 3 ml of the cell-dispersion solution, 3.7 mg of pyridoxal phosphate, and 3 mL of a 1M potassium phosphate buffer (pH 6.8) were introduced. The whole volume was adjusted to 30 mL by adding deionized water therein. This was reacted at 30° C. for 16 hours with stirring. After the reaction is completed, 1-phenyl-3-butylamine thus produced in the reaction mixture was analyzed in the manner described below. This showed that 1-phenyl-3-butylamine was produced with a conversion rate of 68%, and it had a (S) configuration and optical purity of 95.8% e.e.

Workup

  1. customIn the same manner as in Example 12, a cell-dispersion solution was prepared
  2. customInto a flask in which substrates, that is
  3. additionwere introduced
  4. customThis was reacted at 30° C. for 16 hours

Sources & evidence

ORD record
ord-7aa7367d047c4e72ac883857c86664b2
Source dataset
uspto-grants-2013_04
Patent number
US08431378B2

Reaction notes

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