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

HRID 1620275ノート

反応式

HRID 1620275 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-150ac60ebef54ab6bc8653ba62b52f17
出典データセット
uspto-grants-2014_07
特許番号
US08772316B2

反応ノート

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