Abstract
Stereoespecific syntheses of (+/-)-trans-N,N-cyclohexane-1,2-diamines ((+/-)-4 a-g) were carried out from the corresponding (+/-)-trans-N,N-dialkylaminocyclohexanols by successive treatment with mesyl chloride and aqueous ammonia. The stereochemical outcome indicates the formation of a meso-aziridinium ion intermediate. Kinetic resolutions of diamines (+/-)-4 were efficiently accomplished in aminolysis reactions catalyzed by lipase B from Candida antarctica with ethyl acetate as the solvent and acyl donor. Acetamides and the remaining diamines, isolated as the benzyloxycarbonyl derivatives, were obtained with very high ee values (92-99%). One of the carbamates was used as a precursor of the analgesic U-(-)-50,488.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)-cyclohexyl)-benzeneacetamide, (trans)-Isomer / chemical synthesis*
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3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)-cyclohexyl)-benzeneacetamide, (trans)-Isomer / chemistry
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3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)-cyclohexyl)-benzeneacetamide, (trans)-Isomer / metabolism*
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Amines / chemistry
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Analgesics / chemistry*
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Analgesics / metabolism*
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Cyclohexanes / chemistry*
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Diamines / chemistry*
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Enzymes, Immobilized / metabolism*
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Fungal Proteins
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Lipase / metabolism*
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Magnetic Resonance Spectroscopy
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Molecular Structure
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Receptors, Opioid, kappa / antagonists & inhibitors
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Stereoisomerism
Substances
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Amines
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Analgesics
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Cyclohexanes
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Diamines
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Enzymes, Immobilized
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Fungal Proteins
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Receptors, Opioid, kappa
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3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)-cyclohexyl)-benzeneacetamide, (trans)-Isomer
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Lipase
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lipase B, Candida antarctica