Piperidine Carboxylic Acids

G. E. Coates. Chem. and Ind. London) 1941, 185. Theory piperidine-carboxylic acid complexes. 

Ban and coworkers completed a formal total synthesis of vincamine (101) by capitalizing upon the electrochemical oxidation of the piperidine carboxylic acid ester 96 [24]. Thus, when oxidized at a constant current (CCE 30 mA) in methanol at room temperature (Et4NC104 8.2F/mol), 96 was converted to 97, a material that, when treated with formic acid, afforded lactone 98 in a 76% yield after chromatography. Hydrogenation, hydro-... 

S,47 ) -Hydroxypipecolic acid [(-)-a3 -4-hydroxy-2-piperidine carboxylic acid, 3] was isolated from the leaves of Calliandra piuieri and Strophantus scandeus and it was identified as a constituent of cyclopeptide antibiotics, such as virginiamycin S2. It was also employed as a precursor in the preparation of selective N-methyl-D-aspartate receptor antagonists. Furthermore, (-)-3 has served as a building block in a recent synthesis of palinavir, a potent peptidomimetic-based HIV protease inhibitor. ... 

Sorm (48) has described the hydrogenation of picolinic acid in glacial acetic acid with platinum oxide. He was able to obtain the corresponding piperidine carboxylic acid by concentration of the acetic acid solution. Since piperidine-2-carboxylic acid and acetic acid are probably of the same order of acidity, it is likely then that acetic acid is not strong enough to break open the zwitterion form or the hydrogen bonded form of the piperidine acid ... 

Synonyms 1-(3-Hydroxy-3-phenylpropyl)-4-phenyl-4-piperidine-carboxylic acid ethyl ester Trade names Lealzin, Operidine, Phenoperidin... 

Hexahydroisonicotinic Acid (Piperidine- -carboxylic acid, iaonipecotic acid)... 

There ate many examples of piperidine carboxylic acids, prepared by a variety of methods. Reduction of azide 7.278 led to an amine, and subsequent internal Michael addition to the conjugated ester gave methyl 2-(2-piperidino)ethanoate, 7.27P.138... 

The efficient stereodivergent synthesis of cis-(2R,4S)- and fr t i-(2/, 4/ )-4-phos-phonomethyl-2-piperidine carboxylic acid (122) and (123) from the same chiral imine derived from (if)-gliceraldehyde has been elaborated (Scheme 42). ... 

Electrolytic reduction of pyridine-2- and -4-carboxylic acids can be used to give methylpyridines 52 and zinc and acetic acid produce either the methylpyridines or the hydroxymethylpyridines. However, from nicotinic acid the second method produces piperidine, and electrochemical reduction of these acids can be conducted to give piperidine-carboxylic acids, tetrahydropyridine-carboxylic acids and tetrahydro-methylpyridinesi ". ... 

With the piperidine carboxylic acid 42 and two related unhydroxylated amino acids (Boc-4-piperidine carboxylic acid and Boc-i -pipecolic acid) a small library was constructed on a 4-methyl benzhydrylamine resin by use of HATU activation in DMF-dichloromethane 1 1. 

Pulcherrimine is a new sulfur amino acid formally derived from thioglyceric acid and 2-piperidine carboxylic acid. This original compound is responsible for the bitter taste of sea urchin ovaries, which are sometimes... 

Picaridin KBR 3023 1-Piperidine carboxylic acid, 2 (2-hydroxyethyl)-, 1-methylpiopylester 119515-38-7... 

Pipecolic acid (2-piperidine carboxylic acid) is a precursor of various bioactive compounds such as thioridazine (antipsychotic agent), pipradol (anticonvulsant agent), a potassium opioid analgesic, and immunosuppressant FK-506, all of which have been prepared from pij olic acid [149-151]. Ng-Youn-Chem et al. [152] developed an enzymatic pro-... 

---