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Synthesis of some derivatives of alkaloids. XIX

Slovak Academy of Sciences, Bratislava

Abstract: cf. CA 55, 17620a. The synthesis of dl-deoxynupharidine was described. Dehydration of 2-(5-methyl-2-pyridyl)propanol, b0.01 65°, n20D 1.5137, d20 1.023, gave 2-(5-methyl-2-pyridyl)propene (I), b12 76°, n20D 1.5174, d20 0.9485; picrate m. 160-1° (EtOH); hemichloroplatinate m. 171-2° (dil. EtOH). I and CH₂(CO₂Et)₂ in a Michael addn. formed Et 1-carbethoxy-3-(5-methyl-2-pyridyl)valerate, b0.01 120-2°, catalytically hydrogenated with Raney Ni at 300°/140 atm. to 1,7-dimethyl-4-oxoquinolizidine (II), b0.01 88-9°, n20D 1.5042, d20 1.032. II in a Claisen reaction with Et 3-furoate gave 1,7-dimethyl-3-(3-furoyl)-4-oxoquinolizidine (III), b0.01 174-5°, which on acid hydrolysis gave 1-(3-furoyl)-3-(5-methyl-2-piperidyl)butane, b12 150-1°, n20D 1.5593, d20 1.134; picrate m. 144° (EtOH). III was hydrogenated with PtO₂ to 1,7-dimethyl-4-(3-furyl)quinolizidine, b12 127-8°, n20D 1.5144, d20 1.017; HCl salt m. 261-2° (decompn.) (EtOH); picrate m. 173-4° (EtOH); perchlorate m. 193-4° (H₂O). Similarly, 2-(2-pyridyl)propene gave dl-1-methyl-4-(3-furyl)quinolizidine (dl-deoxydemethylnupharidine), b12 122-4°, n20D 1.5124, d20 1.019; picrate m. 171-2° (EtOH); HCl salt m. 257° (decompn.) (EtOH); perchlorate m. 191-2° (H₂O); hemichloroplatinate m. 207-8° (decompn.) (EtOH). 2-Vinylpyridine gave dl-4-(2-furyl)quinolizidine, b11 120-2°, n22D 1.5099, d22 1.023; picrate m. 175° (EtOH).

Full paper in Portable Document Format: 154a283.pdf (in Slovak)

Chemical Papers 15 (4) 283–291 (1961)

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