1. Convenient preparation of optically active cibenzoline and analogues from 3,3-diaryl-2-propen-1-ols
- Author
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Naka Koyata, Takuya Noguchi, Tsuyoshi Miura, Hirohisa Fujimori, Nobuyuki Imai, Hisashi Sasaki, Takuya Nagai, Rie Sato, Masayuki Kirihara, and Yoko Akaiwa
- Subjects
Chemistry ,Cyclopropanation ,Organic Chemistry ,Recrystallization (metallurgy) ,Ethylenediamine ,Optically active ,Medicinal chemistry ,Chloride ,Catalysis ,Inorganic Chemistry ,Hydrolysis ,chemistry.chemical_compound ,Cibenzoline ,medicine ,Organic chemistry ,Physical and Theoretical Chemistry ,medicine.drug - Abstract
( R )-(+)-Cibenzoline (95% ee) was synthesized in two steps from (+)-2,2-diphenylcyclopropylmethanol 3a (98% ee), which was oxidized with IBX in DMSO, followed by treatment with ethylenediamine in the presence of I 2 and K 2 CO 3 in t BuOH. Compound ( R )-(+)- 3a (98% ee) was prepared by cyclopropanation of 3,3-diphenyl-2-propen-1-ol 1 with Et 2 Zn and CH 2 I 2 in the presence of a catalytic amount of ( S )-2-(methanesulfonyl)amino-1-( p -toluenesulfonyl)amino-3-phenylpropane 2 , followed by esterification with 3,5-dinitorobenzoyl chloride, recrystallization, and hydrolysis.
- Published
- 2009
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