Pyridoxal 5'-phosphate → 2-Amino-7-methoxytetralin

HRID 1093906Notes

Reaction equation

HRID 1093906 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=O)[CH2:10]2)=[CH:5][CH:4]=1.CC1[N:20]=CC(COP(O)(O)=O)=C(C=O)C=1O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH:9]([NH2:20])[CH2:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1051Pyridoxal 5'-phosphateHCID 62657Potassium Phosphate, TribasicHCID 777857-Methoxy-2-tetralone

Product 1

HCID 116080152-Amino-7-methoxytetralin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a flask in which substrates, that is, 300 mg of 7-methoxy-2-tetralone and 309.4 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 24 hours with stirring. After the reaction is completed, 7-methoxy-2-aminotetralin thus produced in the reaction mixture was analyzed by HPLC with the conditions described below. This showed that 7-methoxy-2-aminotetralin was produced with a conversion rate of 85%, and it had a (S) configuration and optical purity of 96.7% e.e.

Workup

  1. customInto a flask in which substrates, that is
  2. additionwere introduced
  3. customThis was reacted at 30° C. for 24 hours

Sources & evidence

ORD record
ord-77c85074b6b143f9bbdce79ade598703
Source dataset
uspto-grants-2012_03
Patent number
US08133705B2

Reaction notes

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