Pyridoxal 5'-phosphate → (+-)-3,4-Dimethoxyamphetamine

HRID 1919273Notes

Reaction equation

HRID 1919273 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12](=O)[CH3:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[NH2:27][C@@H](C(O)=O)C.CC1N=CC(COP(O)(O)=O)=C(C=O)C=1O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([NH2:27])[CH3:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 4

HCID 1051Pyridoxal 5'-phosphateHCID 698962-Propanone, 1-(3,4-dimethoxyphenyl)-HCID 71080D-AlanineHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 8423(+-)-3,4-Dimethoxyamphetamine

Procedure

After ten hours in reaction, 1.5 g of a substrate 1-(3,4-dimethoxyphenyl)-2-propanone, 4.17 g of D-glucose, 4.13 g of D-alanine, and 3.3 mg of pyridoxal phosphate were added. During the reaction, the reaction liquid was sampled. From the sample, 1-(3,4-dimethoxyphenyl)-2-aminopropane was extracted by the addition of ethyl acetate after basifying the sample with 6 N aqueous solution of sodium hydroxide. The amount of 1-(3,4-dimethoxyphenyl)-2-aminopropane produced was measured by analyzing 1-(3,4-dimethoxyphenyl)-2-aminopropane under the following HPLC conditions. Further, by the law of the art, 1-(3,4-dimethoxyphenyl)-2-aminopropane thus obtained was acted on by 3,5-dinitrobenzyl chloride to form a dinitrobenzyl derivative. After that, the dinitrobenzyl derivative was analyzed under the following HPLC conditions, whereby the optical purity thereof was measured. In the result, the amount of 1-(3,4-dimethoxyphenyl)-2-aminopropane produced after 27 hours in reaction was 2.42 g. The absolute configuration of 1-(3,4-dimethoxyphenyl)-2-aminopropane was (R), and the optical purity was not less than 99.9% e.e.

Workup

  1. additionwere added
  2. customDuring the reaction
  3. customthe reaction liquid
  4. aliquotwas sampled
  5. extractionFrom the sample, 1-(3,4-dimethoxyphenyl)-2-aminopropane was extracted by the addition of ethyl acetate

Sources & evidence

ORD record
ord-1adaeaf0a8db4842a02db9e7a9a2d81a
Source dataset
uspto-grants-2012_05
Patent number
US08168412B2

Reaction notes

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