- AN EFFICIENT SYNTHESIS OF 3-AMINO-4-FLUOROBUTANOIC ACID, AN INACTIVATOR OF GABA TRANSAMINASE
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3-Amino-4-fluorobutanoic acid (1), a potent in vivo-inactivator of GABA transaminase, is synthesized in two steps.The lithium salt of tert-butyl acetate is condensed with fluoroacetonitrile and the product is reduced with sodium cyanoborohydride in acidic methanol to 1.
- Mathew, Jacob,Invergo, Benedict J.,Silverman, Richard B.
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p. 377 - 384
(2007/10/02)
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- Preparation of fluorinated methyl aminoalkanoic acids and novel process intermediates
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Fluorinated alkenylamines of the Formula V STR1 wherein n represents 0, 1, 2 or 3; R1 represents hydrogen or C1 -C10 alkyl and Y represents (a), when n represents O, CH2 F, (b), when n represents 1, CH2 F or CHF2, or (c) when n represents 2 or 3, CH2 F, CHF2 or CF3 are novel process intermediates. They are obtained by hydrolysis and subsequent reduction of the corresponding alkenyl fluorinated methyl ketimine magnesium halides, which are novel compounds resulting from reaction of the corresponding alkenyl magnesium halides with the corresponding fluorinated acetonitriles. The fluorinated alkenylamines of Formula V are oxidized while the amino group is protected to provide, after removal of the amine protecting group, the corresponding fluorinated methyl aminoalkanoic acids which are useful pharmacological or anti-bacterial agents.
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