Ethanol → (Hexahydro-1H-pyrrolizin-7A-YL)methanamine

Among two types of said reducing reaction, the former type reaction will be completed within 0.5 to 6 hours, when 1 equivalent amount of 7a-nitromethyl-2,3,5,6,7,7a-hexahydro-1H-pyrrolizine or a salt thereof and 3 to 10 equivalent amount of the acid and 3 to 10 equivalent amount of the metal or the metal salt were dissolved in a suitable solvent to stir the mixture at room temperature. As the solvent, methanol, ethanol, n-propanol, i-propanol or the like alcohol; water; or a mixture of water and an alcohol may be listed. After completion of the reaction, insoluble matters were filtered off, the filtrate was, if necessary, concentrated in vacuo, adding thereto an alkali solution, filtering off, if necessary, insoluble matters, distilling out the solvent, extracting with use of an organic solvent, concentrating the extract, and distilling the residue; or after completion of the reaction, an alkali carbonate or a solution thereof was added to the reaction mixture, filtering off formed insoluble matters, concentrating the filtrate in vacuo, dissolving or suspending the resulting residue in an organic solvent, stirring same for 1 to 12 hours at 20° C., while introducing ammonia gas, filtering-off insoluble matters, concentrating the filtrate in vacuo, and then distilling in vacuo to afford the desired 7a-aminomethyl-2,3,5,6,7,7a-hexahydro-1H-pyrrolizine (Compound III). As the alkali for alkalidizing the reaction mixture, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate or the like may be listed. As the extraction solvent, methylene chloride, chloroform, ethyl ether, ethyl acetate or the like may be listed. While, as the basic carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, calcium carbonate or the like may be listed. As the organic solvent for dissolving or suspending the residue, benzene, toluene, tetrahydrofuran, dioxane or the like ether solvent; methanol, ethanol, i-propanol, n-propanol, i-butanol, n-butanol or the like alcoholic solvent may be listed.

1. customreaction
2. customthe former type reaction
3. customAfter completion of the reaction, insoluble matters
4. filtrationwere filtered off
5. concentrationif necessary, concentrated in vacuo
6. additionadding
7. filtrationan alkali solution, filtering off
8. distillationif necessary, insoluble matters, distilling out the solvent
9. extractionextracting with use of an organic solvent
10. concentrationconcentrating the extract
11. distillationdistilling the residue
12. customor after completion of the reaction
13. filtrationfiltering off
14. customformed insoluble matters
15. concentrationconcentrating the filtrate in vacuo
16. dissolutiondissolving
17. stirringstirring same for 1 to 12 hours at 20° C.
18. additionwhile introducing ammonia gas
19. concentrationfiltering-off insoluble matters, concentrating the filtrate in vacuo
20. distillationdistilling in vacuo

ORD 기록

ord-08542679003144008accc046bd7085b6

출처 데이터셋

uspto-grants-1991_01

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US04985569