By R.H.F Manske, H.L. Holmes
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Extra resources for Alkaloids: v. 3: Chemistry and Pharmacology
CLXXIX ester (CLXXVIII) and obtained an aminoketone (CLXXIX) which was reduced to the corresponding aminoalcohol in the presence of palladium black. The extensive further literature on the preparation of S n a l O g U e S possessing the ethanolamine structure characteristic of the cinchona 44 RICHARD B. TURNER AND R. B. WOODWARD bases is mentioned here only briefly. In 1917 Karrer (215) carried out the reaction of cinchoninyl chloride hydrochloride with pyrrylmagnesium iodide and obtained 4-quinoly1-(2-pyrryl)-ketoneJwhich on reduction with zinc dust and acid furnished the quinolylpyrrylcarbinol (CLXXX).
TEE QUINUCLIDINE The synthetic investigations related to the quinuclidine moiety had as their first objectives the synthesis of simple quinuclidine derivatives and degradation products from the alkaloids. In 1904, Koenigs showed that B-collidine (CXLVII), which was at that time available only from the degradation of cinchonine (47, 58, 59), could be condensed with formaldehyde to give 3ethyl4@-hydroxyethyl)-pyridine (CXLVIII), which on reduction with sodium and alcohol THB1 CHEMISTRY OF THE CINCHONA ALKALOIDS 39 CHaCHaOH H CXLVIE CXLVIII CXLIX yielded the corresponding hexahydro derivative (CXLIX) (191).
The latter substance was converted by zinc and acetic acid into CHIC0tC&& CHiCHa - H CHtCHtOH H CVII CVIII CH,CH& CHICHI 6 €I CIX CHICHI CHICHI + 6 H cx 4 THBl CHEMISTRY OF TEE CINCHONA ALKALOIDS CXI CHaCH: CHrCH: 0- 27 CXII - (5 HaCH: CHrCH: COOH CXIII CXIV 3,Methylpiperidine (CX), which on von Braun degradation yielded the dibromo derivative (CXI). The dibromide was then coupled with malonic ester, and saponification and decarboxylation of the resulting dicarboxylic ester (CXII) afforded optically active diethylcyclohexanecarboxylic acid (CXIII).