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Preparation and Muscarinic Antagonism of Optically Active p-Fluorohexahydro-sila-diphenidol

Research Project

Project/Area Number 07651026
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 有機工業化学
Research InstitutionSaitama University

Principal Investigator

TERUNUMA Daiyo  Saitama Univ., Engineering, Associate Prof., 工学部, 助教授 (10008857)

Project Period (FY) 1995 – 1996
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1996: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1995: ¥1,800,000 (Direct Cost: ¥1,800,000)
Keywordsp-F-HHSiD / Optical resolution / Muscarinic antagonism / 抗ムスカリン剤 / 生理活性有機ケイ素 / 光学活性有機ケイ素
Research Abstract

1.Although, a diastereomer of p-Fluorohexahydro-sila-diphenidol (p-F-HHSiD) precursor with optically active menthol did not crystallize, it was found that diastereomer of p-F-HHSiD precursor with (-) -cholesterol crystallized. Recrystallization of the the diastereomer from pentane was carried out several times to gave optically pure diastereomer in 25% yield.
2.Reduction of the diastereomer obtained was reduced with lithium aluminum hydride to give an optically active hydrosilane derivative. Then, the derivative was reacted successfully with potassium hydroxide to yield (+) -p-F-HHSiD in a high optical purity.
3.Unfortunately, we did not succeed to obtain the antipode ; (-) -p-F-HHSiD,by fractional crystallization method, because it is difficult to use the resolving agent ; (+) -cholesterol, for the antipode. It was found, however, that methyl iodide derivative of (+) -p-F-HHSiD in 70% o.p.was enriched to over 95% o.p.by recrystallization.
4.It is necessary to prepare both enantiomers of p-F-HHSiD in high optical purities to investigate muscarinic antagonism. Now, we are concentrating our efforts to improve the optical purity of methyl iodide derivative of (-) -p-F-HHSiD by a recrystallization method.

Report

(3 results)
  • 1996 Annual Research Report   Final Research Report Summary
  • 1995 Annual Research Report

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Published: 1995-04-01   Modified: 2016-04-21  

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