tert-Butyldimethylsilyl chloride → 3-(Tert-butyldimethylsilyloxy)-4-iodo-6,7-dimethoxy-1-propylisoquinoline

HRID 1620275노트

반응식

HRID 1620275 반응식
[I:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([CH2:16][CH2:17][CH3:18])=[N:4][C:3]=1[OH:19].CC(N(C(C)C)CC1C=CC=CC=1)C.C=CC1C=CC=CC=1.C=CC1C=CC(C=C)=CC=1.[C:52]([Si:56](Cl)([CH3:58])[CH3:57])([CH3:55])([CH3:54])[CH3:53]>C(Cl)Cl>[Si:56]([O:19][C:3]1[N:4]=[C:5]([CH2:16][CH2:17][CH3:18])[C:6]2[C:11]([C:2]=1[I:1])=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][CH3:15])[CH:7]=2)([C:52]([CH3:55])([CH3:54])[CH3:53])([CH3:58])[CH3:57]

참가 물질

5

반응물 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 16212447N-benzyl-N-propan-2-ylpropan-2-amine;1,4-bis(ethenyl)benzene;styreneHCID 1784402504-Iodo-6,7-dimethoxy-1-propylisoquinolin-3-ol

생성물 1

HCID 681823083-(Tert-butyldimethylsilyloxy)-4-iodo-6,7-dimethoxy-1-propylisoquinoline수율 83%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of 4-iodo-6,7-dimethoxy-1-propylisoquinolin-3-ol CCH 42098-1 (0.60 g, 1.61 mmol) and diisopropylaminomethyl-polystyrene resin (3 mmol/g, 0.80 g, 2.40 mmol) in dry CH2Cl2 (16 mL) in a 50 mL round-bottomed flask equipped with a magnetic stirrer was added tert-butylchlorodimethylsilane (267 mg, 1.77 mmol) and the reaction mixture was stirred for 15 min at RT then for 1 h under reflux. After cooling to RT, the reaction mixture was filtered and the filtrate was washed with brine (5 mL), dried over Na2SO4, filtered and concentrated at 40° C. under vacuum. Purification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 95:5) gave 3-(tert-butyldimethylsilyloxy)-4-iodo-6,7-dimethoxy-1-propylisoquinoline CCH 42098-2 as an off-white solid (0.65 g, 83% yield).

후처리

  1. customequipped with a magnetic stirrer
  2. temperaturefor 1 h under reflux
  3. temperatureAfter cooling to RT
  4. filtrationthe reaction mixture was filtered
  5. washthe filtrate was washed with brine (5 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated at 40° C. under vacuum
  9. customPurification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 95:5)

출처 및 근거

ORD 기록
ord-150ac60ebef54ab6bc8653ba62b52f17
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772316B2

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