Reaktion #82168

ord-b08cfe36bb5245e6ae1df9bbdef71642

Reaktionsgleichung

CC(=O)OC1C=CC(=O)N2CC(OC(C)=O)C(OC(C)=O)C12
(1S,2R,8R,8aR)-1,2,8-triacetoxy-1,2,3,5,8,8a-hexahydro-5-oxyindolizine
[H][H]
hydrogen
→
CC(=O)O[C@H]1[C@H]2[C@H](OC(C)=O)CCC(O)N2C[C@H]1OC(C)=O
(1S,2R,8R,8aR)-1,2,8-triacetoxy-octahydro-5-oxyindolizine

Edukte

CC(=O)OC1C=CC(=O)N2CC(OC(C)=O)C(OC(C)=O)C12
(1S,2R,8R,8aR)-1,2,8-triacetoxy-1,2,3,5,8,8a-hexahydro-5-oxyindolizine
[H][H]
hydrogen

Reagenzien

Keine

Lösungsmittel

CCO
ethanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationThe catalyst was filtered
  2. 2
    Sonstigethe filtrate was evaporated to dryness
  3. 3
    Filtrationhexane and filtered

Vorschrift

14. (1S,2R,8R,8aR)-1,2,8-triacetoxy-1,2,3,5,8,8a-hexahydro-5-oxyindolizine, 13, 22 g (0.070 mole), was hydrogenated at atmospheric pressure of hydrogen in 400 mL ethanol containing 3 g 10% Pd on carbon. The reaction was allowed to proceed overnight. The catalyst was filtered, and the filtrate was evaporated to dryness. The crystalline residue was taken up in ether and hexane and filtered to afford (1S,2R,8R,8aR)-1,2,8-triacetoxy-octahydro-5-oxyindolizine, 14, 21.4 g (0.068 mole; 97%) as a white crystalline solid of m.p. 146°-147° C. (lit. 143-145 ; A. C. Richardson et. al., Carb. Res., 136: 225(1985)).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05621106uspto-grants-1997_04