Pyridoxal 5'-phosphate → 1-Benzyl-3-aminopyrrolidine

HRID 1970759Notes

Reaction equation

HRID 1970759 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10](=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1[N:20]=CC(COP(O)(O)=O)=C(C=O)C=1O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([NH2:20])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1051Pyridoxal 5'-phosphateHCID 62657Potassium Phosphate, TribasicHCID 698901-Benzyl-3-pyrrolidinone

Product 1

HCID 27566131-Benzyl-3-aminopyrrolidine

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, 900 mg of 1-benzyl-3-pyrrolidinone and 928.2 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-benzyl-3-aminopyrrolidine thus produced in the reaction mixture was analyzed via HPLC with the conditions described below. This showed that 1-benzyl-3-aminopyrrolidine was produced with a conversion rate of 75.1%, and it had a (S) configuration and optical purity of 79.2% 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-788e9ab3c3994ab9866ff40b33f069e7
Source dataset
uspto-grants-2013_04
Patent number
US08431378B2

Reaction notes

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