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US 8,148,549 B2Granted
Preparation of (S)-(+)-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl) propylamine using optically active methylhydroxylaminopropanol compound as an intermediate
AssigneeSCI Pharmtech, Inc.
InventorsBo-Fong Chen, Jinun-Ban Yeh, Wei-Chyun Wong
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Abstract
The present invention provides a (S)-methylhydroxylaminopropanol derivative as an intermediate for preparation of (S)-(+)-N-methyl-3-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine. The present invention also provides a process for preparing (S)-(+)-N-methyl-3-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine with higher yield and lower cost, wherein the (S)-methylhydroxylaminopropanol derivative is used as an intermediate.
Claims15
A process for preparing (+)-(S)-N-methyl-3 -(1 -naphthyloxy)-3 -(2-thienyl) propylamine, comprising steps of:
- (i) performing a Mannich reaction of 2-acetylthiophene, formaldehyde and a methylhydroxylamine of formula, HNCH3(OR), to form a substituted amino ketone of formula (I)
- (ii) reducing the substituted amino ketone of formula (I) enatio selectively to a (S)-methylhydroxylaminopropanol compound of formula (II)
- (iii) performing a reaction of the (S)-methylhydroxylaminopropanol compound of formula (II) with halonaphthalene to form N-methyl-N-hydroxyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine compound
- (iv) performing an N, O-cleavage reaction of the N-methyl-N-hydroxyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine compound (III) to form (+)-(S)-N-methyl-3-(1-naphthyloxy)-3-(2-thienyl) propylamine,
- wherein R is a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or an aryl group having 6 to 10 carbon atoms.
2 more elements
Dependencies are inferred from the claim text.