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

HRID 1369601노트

반응식

HRID 1369601 반응식
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:15][C@@H:14]2[C@@H:9]([CH2:10][CH2:11][C@H:12]([CH2:16][N:17]3[CH:21]=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:19]=[CH:18]3)[CH2:13]2)[CH2:8][N:7]1C(OC)=O)=[O:5])[CH3:2].C[Si](I)(C)C>C(Cl)Cl>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:15][C@@H:14]2[C@@H:9]([CH2:10][CH2:11][C@H:12]([CH2:16][N:17]3[CH:21]=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:19]=[CH:18]3)[CH2:13]2)[CH2:8][NH:7]1)=[O:5])[CH3:2]

참가 물질

4

반응물 2

HCID 85247Trimethylsilyl iodideHCID 11048093[3S,4aR,6S,8aR]-ethyl-6-((4-ethoxycarbonyl-1H-imidazol-1-yl)methyl)-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate

생성물 1

HCID 9799112[3S,4aR,6S,8aR]-Ethyl-6-((4-Ethoxycarbonyl-1H-Imidazol-1-yl)Methyl)-1,2,3,4,4a,5,6,7,8,8a-Decahydroisoquinoline-3-Carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 0.90 g of [3S,4aR,6S,8aR]-ethyl-6-((4-ethoxycarbonyl-1H-imidazol-1-yl)methyl)-2-(methoxycarbonyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate in 20 ml of methylene chloride was added 1.5 ml trimethylsilyl iodide. The reaction was stirred at room temperature for six hours, quenched with excess absolute ethanol and evaporated to dryness. The residue was purified by strong cation exchange chromatography eluting with 10-50% methanol in chloroform followed by 50% 2M ammonia/methanol in chloroform to provide the final title compound, [3S,4aR,6S,8aR]-ethyl-6-((4-ethoxycarbonyl-1H-imidazol-1-yl)methyl)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate.

후처리

  1. customquenched with excess absolute ethanol
  2. customevaporated to dryness
  3. customThe residue was purified by strong cation exchange chromatography
  4. washeluting with 10-50% methanol in chloroform

출처 및 근거

ORD 기록
ord-3f5c5eb8124247edad30f4c79a1aeaea
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06579886B2

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