Methylamine → Pseudoephedrine

HRID 1033721Notes

Reaction equation

[CH3:1][C@H:2]([NH:11][CH3:12])[C@H:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CN>>[CH3:1][C@H:2]([NH:11][CH3:12])[C@@H:3]([OH:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

Reactant 2

HCID 6329Methylamine

HCID 9294Ephedrine3×

Product 1

HCID 7028Pseudoephedrine

Procedure

The combination of yeast transformation of benzaldehyde to produce PAC and chemical conversion of the PAC to make l-ephedrine is described in U.S. Pat. No. 1,956,950. The PAC can be converted by a chemical reductive amination with methylamine to optically pure L-ephedrine as follows: ##STR2## The l-ephedrine can then converted in high yield to d-pseudoephedrine as follows: ##STR3## It is apparent from this reaction scheme that microbial transformation of benzaldehyde by yeast to form L-(-)phenyl acetyl carbinol in high yield and purity is of prime importance for successful commercial operation of the synthetic route.

Sources & evidence

ORD record: ord-4604d30c17884f08952811795c28158b
Source dataset: uspto-grants-1994_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05312742

Reaction notes

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