Lithium Hydroxide → (E)-(3S,8aR)-3-(4-chlorophenyl)-6-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]hexahydroindolizin-5-one

HRID 16345노트

반응식

HRID 16345 반응식
[OH-].[Li+].O1CCCC1.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[N:18]1[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19]1)[CH:13]=O.C(OP([CH:32]1[CH2:40][CH2:39][C@@H:38]2[N:34]([C@H:35]([C:41]3[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=3)[CH2:36][CH2:37]2)[C:33]1=[O:48])(=O)OCC)C>O.C(O)C>[Cl:47][C:44]1[CH:43]=[CH:42][C:41]([C@H:35]2[N:34]3[C@H:38]([CH2:39][CH2:40]/[C:32](=[CH:13]\[C:12]4[CH:15]=[CH:16][C:17]([N:18]5[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19]5)=[C:10]([O:9][CH3:8])[CH:11]=4)/[C:33]3=[O:48])[CH2:37][CH2:36]2)=[CH:46][CH:45]=1

참가 물질

7

반응물 4

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 272824453-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehydeHCID 86612704diethyl[(3S,8aR)-3-(4-chlorophenyl)-5-oxooctahydroindolizin-6-yl]phosphonate

생성물 1

HCID 68717808(E)-(3S,8aR)-3-(4-chlorophenyl)-6-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]hexahydroindolizin-5-one수율 78.9%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

Lithium hydroxide (355 mg) was added to a solution mixture of tetrahydrofuran (8 mL)-ethanol (30 mL) of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (875 mg) and [(3S,8aR)-3-(4-chlorophenyl)-5-oxooctahydroindolizin-6-yl]phosphonic acid diethyl ester (2.5 g). The resulting reaction solution was stirred under light-shielded conditions at room temperature for 5 hr and then poured into iced-water. The resulting mixture was extracted with ethyl acetate. The extract solution was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane-ethyl acetate system) to give 1.43 g of the title compound as a colorless solid. The physical property values of this compound were as follows:

후처리

  1. customThe resulting reaction solution
  2. extractionThe resulting mixture was extracted with ethyl acetate
  3. washThe extract solution was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (heptane-ethyl acetate system)

출처 및 근거

ORD 기록
ord-fba512a2cdc34ccb9e41ce6e0adba248
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737141B2

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