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 1369598ノート

反応式

HRID 1369598 の反応式
[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]

参加物

6

反応物 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、化合物

生成物 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-Carboxylate収率 49.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
20 °C

実験手順

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);

後処理

  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

出典と根拠

ORDレコード
ord-3b3ecb52523d40a8b14725a419047aed
出典データセット
uspto-grants-2003_06
特許番号
US06579886B2

反応ノート

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