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)
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
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.