Sodium borohydride → 6-Methoxy-1-[1-(1-methyl-1H-imidazole-4-sulfonyl)-piperidin-4-yl]-1,2,3,4-tetrahydroisoquinoline

HRID 397064

반응식

HRID 397064 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH:13]1[CH2:18][CH2:17][N:16]([S:19]([C:22]3[N:23]=[CH:24][N:25]([CH3:27])[CH:26]=3)(=[O:21])=[O:20])[CH2:15][CH2:14]1)=[N:8][CH2:7][CH2:6]2.[BH4-].[Na+]>CO.O.C([O-])(O)=O.[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([CH:13]1[CH2:18][CH2:17][N:16]([S:19]([C:22]3[N:23]=[CH:24][N:25]([CH3:27])[CH:26]=3)(=[O:21])=[O:20])[CH2:15][CH2:14]1)[NH:8][CH2:7][CH2:6]2

참가 물질

6

반응물 2

HCID 4311764Sodium borohydrideHCID 181724606-Methoxy-1-[1-(1-methyl-1H-imidazole-4-sulfonyl)-piperidin-4-yl]-3,4-dihydro-isoquinoline

생성물 1

HCID 181724296-Methoxy-1-[1-(1-methyl-1H-imidazole-4-sulfonyl)-piperidin-4-yl]-1,2,3,4-tetrahydroisoquinoline수율 71.6%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a stirred solution of 6-methoxy-1-[1-(1-methyl-1H-imidazole-4-sulfonyl)-piperidin-4-yl]-3,4-dihydro-isoquinoline (0.077 g, 0.197 mmol) in MeOH (3 ml) cooled to 0° C. was added NaBH4. The reaction mixture was then stirred at RT for 2 hours and diluted with water (5 ml) and sat. NaHCO3 (5 ml). The mixture was extracted with EtOAc (3×10 ml). The combined organics were washed with brine (1×10 ml), dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by radial chromatography (SiO2, 1 mm, CH2Cl2 to 5% MeOH/CH2Cl2) to give the product as an oil (0.055 g, 0.141 mmol, 71% yield).

후처리

  1. extractionThe mixture was extracted with EtOAc (3×10 ml)
  2. washThe combined organics were washed with brine (1×10 ml)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by radial chromatography (SiO2, 1 mm, CH2Cl2 to 5% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-44e81755739f48caaea3a7be78b51332
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06608203B2

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