Reaktionsgleichung
O=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][C:8]([OH:10])=O.[NH3:11]>[Ni].[H][H]>[O:10]=[C:8]1[NH:11][CH:2]2[CH2:6][CH2:5][CH2:4][CH:3]2[CH2:7]1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Heat under reflux cis-octahydrocyclopenta[b]pyrrole [prepared by the methods of A. Bertho, et al, Chem. Ber. 92, 2218 (1959), wherein 2-oxo-cyclopentyl acetic acid is cyclized by reduction with Raney Nickel/H2 in the presence of ammonia to obtain 2-keto-octahydrocyclopenta[b]pyrrole, which is then reduced with lithium aluminum hydride in etheral solution to yield cis-octahydrocyclopenta[b]pyrrole, or by the method of A. G. Anderson, Jr., et al, J. Org. Chem. 43, 55 (1978), discussed above] and mercuric acetate in water or up to 10% aqueous acetic acid for twenty hours or more, to obtain cis-3,3a,4,5,6,6a-hexahydrocyclopenta[b]pyrrole. Dissolve this compound in water and treat with potassium cyanide followed by 2N hydrochloric acid at 0° C. for two hours and at room temperature for approximately twenty hours to obtain 2-cyano-cis-octahydrocyclopenta[b]pyrrole. Heat this resultant compound in 6N hydrochloric acid under reflux for 6 hours followed by concentration of the reaction mixture to obtain cis-octahydrocyclopenta[b]pyrrole-2-carboxylic acid. If desired, adsorb the residue on an XAD-2 resin column and elute with methanol. Esterify by reaction with ethanol to obtain ethyl cis-octahydrocyclopenta[b]pyrrole-2-carboxylate, as a mixture of two epimers.
Aufarbeitung
- temperatureHeat under reflux cis-octahydrocyclopenta[b]pyrrole [
- customprepared by the methods of A
Quellen und Nachweise
- ORD-Eintrag
- ord-f7f278b1950446c68c26d91d9c1f2ce2
- Quelldatensatz
- uspto-grants-1989_05
- Patentnummer
- US04831157
Verknüpfte Notizen
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