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)

Takashi YANAGI; Ken KIKUCHI; Hideki TAKEUCHI; Takehiro ISHIKAWA; Toshihiro NISHIMURA; Iwao YAMAMOTO

doi:10.1248/cpb.49.1018

Regular Articles

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)

Takashi YANAGI, Ken KIKUCHI, Hideki TAKEUCHI, Takehiro ISHIKAWA, Toshihiro NISHIMURA, Iwao YAMAMOTO

Author information

Keywords: KUR-1246, β2-adrenoceptor agonist, uterine relaxant, asymmetric borane reduction

JOURNAL FREE ACCESS

2001 Volume 49 Issue 8 Pages 1018-1023

DOI https://doi.org/10.1248/cpb.49.1018

Details

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-tetrahydronaphthalen-7-yl]oxy}-N, N-dimethylacetamide) sulfate (KUR-1246), was established by the coupling of optically active components, the bromohydrin 14 and the amine 24. We now describe the practical synthesis of these two optically active components. Bromohydrin 14 was obtained by the asymmetric borane reduction of the prochiral phenacyl bromide 13 using a catalyst prepared from aluminum triethoxide and a chiral amino alcohol. The other optically active component 24 was prepared from (S)-AMT.

Corresponding author

Register with J-STAGE for free!