(1,8-diacetyloxy-5-oxo-2,3,8,8a-tetrahydro-1H-indolizin-2-yl) acetate → [(1S,2R,8R,8aR)-1,2-diacetyloxy-5-hydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-8-yl] acetate

HRID 129108Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 129108
[CH3:1][C:2]([O:4][CH:5]1[CH:9]([O:10][C:11]([CH3:13])=[O:12])[CH:8]2[CH:14]([O:19][C:20]([CH3:22])=[O:21])[CH:15]=[CH:16][C:17](=[O:18])[N:7]2[CH2:6]1)=[O:3].[H][H]>C(O)C>[CH3:22][C:20]([O:19][C@H:14]1[C@@H:8]2[C@H:9]([O:10][C:11]([CH3:13])=[O:12])[C@H:5]([O:4][C:2]([CH3:1])=[O:3])[CH2:6][N:7]2[CH:17]([OH:18])[CH2:16][CH2:15]1)=[O:21]

Komponenten

4

Edukt 2

HCID 19045964(1,8-diacetyloxy-5-oxo-2,3,8,8a-tetrahydro-1H-indolizin-2-yl) acetateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 49759897[(1S,2R,8R,8aR)-1,2-diacetyloxy-5-hydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-8-yl] acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

(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)).

Aufarbeitung

  1. filtrationThe catalyst was filtered
  2. customthe filtrate was evaporated to dryness
  3. filtrationhexane and filtered

Quellen und Nachweise

ORD-Eintrag
ord-2b86cbfc24da46a380b88b90b6ab2fc3
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05466809

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