Dimethylformamide → [3S,4aR,6S,8aR]-Ethyl-6-((4-Ethoxycarbonyl-5-Methyl-1H-Imidazol-1-yl)Methyl)-2-(Methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-Decahydroisoquinoline-3-Carboxylate

HRID 1369598노트

반응식

HRID 1369598 반응식
[H-].[Na+].[CH3:3][C:4]1[N:5]=[CH:6][NH:7][C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].CN(C=O)C.[CH2:19]([O:21][C:22]([C@@H:24]1[CH2:33][C@@H:32]2[C@@H:27]([CH2:28][CH2:29][C@H:30]([CH2:34]OS(C3C=CC=C([N+]([O-])=O)C=3)(=O)=O)[CH2:31]2)[CH2:26][N:25]1[C:48]([O:50][CH3:51])=[O:49])=[O:23])[CH3:20]>C1COCC1>[CH2:19]([O:21][C:22]([C@@H:24]1[CH2:33][C@@H:32]2[C@@H:27]([CH2:28][CH2:29][C@H:30]([CH2:34][N:5]3[C:4]([CH3:3])=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:7]=[CH:6]3)[CH2:31]2)[CH2:26][N:25]1[C:48]([O:50][CH3:51])=[O:49])=[O:23])[CH3:20]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 10994514[3S,4aR,6S,8aR]-ethyl-6-((3-nitrophenylsulfonyloxy)methyl)-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylateHCID 178470400HCID 178470400, 화합물

생성물 1

HCID 11224329[3S,4aR,6S,8aR]-Ethyl-6-((4-Ethoxycarbonyl-5-Methyl-1H-Imidazol-1-yl)Methyl)-2-(Methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-Decahydroisoquinoline-3-Carboxylate수율 49.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
20 °C

실험 절차

Sodium hydride (0.24 g, 1.2 eq) was washed with hexanes (3×10 ml) and suspended in dry THF (10 ml). To this was added a solution of 0.848 g of ethyl 4-methyl-5-imidazolecarboxylate in THF (5 ml) dropwise. The reaction mixture was stirred at 20° C. for 1.5 h and DMF (10 ml) was added. To the resulting solution was slowly added a solution of 2.43 g of [3S,4aR,6S,8aR]-ethyl-6-((3-nitrophenylsulfonyloxy)methyl)-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate in THF (10 ml). The reaction was stirred at ambient temperature over night under N2. The reaction was quenched with saturated aqueous sodium bicarbonate. The resulting white solid was removed by filtration and the filtrate was extracted with ethyl acetate (3×10 ml). The combined organic extract was washed with brine, dried (MgSO4), filtered, and evaporated to a light brown oil. The crude product was chromatographed over silica gel eluting with ethyl acetate to give 1.09 g of the intermediate title compound: MS m/z: 456.3 (m++1);

후처리

  1. stirringThe reaction was stirred at ambient temperature over night under N2
  2. customThe reaction was quenched with saturated aqueous sodium bicarbonate
  3. customThe resulting white solid was removed by filtration
  4. extractionthe filtrate was extracted with ethyl acetate (3×10 ml)
  5. extractionThe combined organic extract
  6. washwas washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated to a light brown oil
  10. customThe crude product was chromatographed over silica gel eluting with ethyl acetate

출처 및 근거

ORD 기록
ord-3b3ecb52523d40a8b14725a419047aed
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06579886B2

반응 노트

불러오는 중…