(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 129108노트

반응식

HRID 129108 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

(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)).

후처리

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

출처 및 근거

ORD 기록
ord-2b86cbfc24da46a380b88b90b6ab2fc3
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05466809

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