Reacción #2006455

ord-1adaeaf0a8db4842a02db9e7a9a2d81a

Ecuación de reacción

COc1ccc(CC(C)=O)cc1OC
1-(3,4-dimethoxyphenyl)-2-propanone
O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
D-glucose
C[C@@H](N)C(=O)O
D-alanine
Cc1ncc(COP(=O)(O)O)c(C=O)c1O
pyridoxal phosphate
COc1ccc(CC(C)N)cc1OC
1-(3,4-dimethoxyphenyl)-2-aminopropane

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONwere added
  2. 2
    OtroDuring the reaction
  3. 3
    Otrothe reaction liquid
  4. 4
    workup.ALIQUOTwas sampled
  5. 5
    ExtracciónFrom the sample, 1-(3,4-dimethoxyphenyl)-2-aminopropane was extracted by the addition of ethyl acetate

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08168412B2uspto-grants-2012_05