تفاعل #82168

ord-b08cfe36bb5245e6ae1df9bbdef71642

معادلة التفاعل

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

المتفاعلات

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

الكواشف

لا شيء

المذيبات

CCO
ethanol

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    ترشيحThe catalyst was filtered
  2. 2
    أخرىthe filtrate was evaporated to dryness
  3. 3
    ترشيحhexane and filtered

الإجراء التجريبي

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)).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05621106uspto-grants-1997_04