1996 Fiscal Year Final Research Report Summary
Preparation and Muscarinic Antagonism of Optically Active p-Fluorohexahydro-sila-diphenidol
| Project/Area Number |
07651026
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
有機工業化学
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| Research Institution | Saitama University |
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Principal Investigator |
TERUNUMA Daiyo Saitama Univ., Engineering, Associate Prof., 工学部, 助教授 (10008857)
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| Project Period (FY) |
1995 – 1996
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| Keywords | p-F-HHSiD / Optical resolution / Muscarinic antagonism |
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| 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.
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