The practical synthesis of a uterine relaxant, bis(2-{[(2S)-2-({(2R)-2-hydroxy-2-[4-hydroxy-3-(2-hydroxyethyl)-phenyl]ethyl}amino)-1,2,3,4-tetrahydronaphthalen-7-yl]oxy}-N,N-dimethylacetamide) sulfate (KUR-1246)

Citation
T. Yanagi et al., The practical synthesis of a uterine relaxant, bis(2-{[(2S)-2-({(2R)-2-hydroxy-2-[4-hydroxy-3-(2-hydroxyethyl)-phenyl]ethyl}amino)-1,2,3,4-tetrahydronaphthalen-7-yl]oxy}-N,N-dimethylacetamide) sulfate (KUR-1246), CHEM PHARM, 49(8), 2001, pp. 1018-1023
Citations number
14
Categorie Soggetti
Chemistry & Analysis
Journal title
CHEMICAL & PHARMACEUTICAL BULLETIN
ISSN journal
00092363 → ACNP
Volume
49
Issue
8
Year of publication
2001
Pages
1018 - 1023
Database
ISI
SICI code
0009-2363(200108)49:8<1018:TPSOAU>2.0.ZU;2-A
Abstract
The synthetic route for a uterine relaxant, bis(2-{[(2S)-2-({(2R)-2-hydroxy -2-[4-hydroxy-3-(2-hydroxyethyl)phenyl]ethyl}amino)-1,2,3,4-tetrahydronapht halen-7-yl]oxy}N,N-dimethylacetamide) sulfate (KUR-1246), was established b y the coupling of optically active components, the bromohydrin 14 and the a mine 24. We now describe the practical synthesis of these two optically act ive components. Bromohydrin 14 was obtained by the asymmetric borane reduct ion of the prochiral phenacyl bromide 13 using a catalyst prepared from alu minum triethoxide and a chiral amino alcohol. The other optically active co mponent 24 was prepared from (S)-AMT.