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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1919273Generated: November 2, 2026

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

https://huagongshe.com/reaction/1919273

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPyridoxal 5'-phosphateHCID 1051—
Reactant2-Propanone, 1-(3,4-dimethoxyphenyl)-HCID 69896—
ReactantD-AlanineHCID 71080—
Reactant(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 107526—
Product(+-)-3,4-DimethoxyamphetamineHCID 8423—

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08168412B2
Source datasetuspto-grants-2012_05
ORD IDord-1adaeaf0a8db4842a02db9e7a9a2d81a
Source noteuspto-grants-2012_05