Iodoethane → (R)-2-[1-(4-bromo-2,6-dimethylphenyl)-3,5-diethyl-1H-pyrazol-4-ylmethyl]-3-ethoxymethyl-1,2,3,4-tetrahydro-isoquinoline

HRID 1740104ノート

反応式

HRID 1740104 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:13]([CH2:14][CH3:15])=[C:12]([CH2:16][N:17]3[C@@H:26]([CH2:27][OH:28])[CH2:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:18]3)[C:11]([CH2:29][CH3:30])=[N:10]2)=[C:4]([CH3:31])[CH:3]=1.[H-].[Na+].[CH2:34](I)[CH3:35]>O1CCCC1>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N:9]2[C:13]([CH2:14][CH3:15])=[C:12]([CH2:16][N:17]3[C@@H:26]([CH2:27][O:28][CH2:34][CH3:35])[CH2:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:18]3)[C:11]([CH2:29][CH3:30])=[N:10]2)=[C:4]([CH3:31])[CH:3]=1

参加物

5

反応物 3

HCID 6340IodoethaneHCID 24758Sodium hydride3 回HCID 54272289(R)-{2-[1-(4-Bromo-2,6-dimethylphenyl)-3,5-diethyl-1H-pyrazol-4-yl methyl]-1,2,3,4-tetrahydro-isoquinolin-3-yl}-methanol

生成物 1

HCID 53638919(R)-2-[1-(4-bromo-2,6-dimethylphenyl)-3,5-diethyl-1H-pyrazol-4-ylmethyl]-3-ethoxymethyl-1,2,3,4-tetrahydro-isoquinoline収率 141.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To an ambient temperature solution of (R)-{2-[1-(4-bromo-2,6-dimethylphenyl)-3,5-diethyl-1H-pyrazol-4-ylmethyl]-1,2,3,4-tetrahydro-isoquinolin-3-yl }-methanol (0.45 g, 0.93 mmol) in anhydrous tetrahydrofuran (12 ml) was added sodium hydride (224 mg of 60% sodium hydride mineral oil dispersion; 5.6 mmol of sodium hydride was added. After stirring for 5 minutes, ethyl iodide (0.37 ml, 4.7 mmol) was added all at once. The reaction mixture was then stirred for 21 hours. The solvent was removed in vacuo, and the remaining residue was extracted with ethyl acetate/water (10 ml of each). The aqueous phase was separated, and then extracted twice with equal volumes of fresh ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo to afford a yellow oil (0.67 g). Flash chromatography (silica gel, 40 micron mesh; elution with ethyl acetate/hexane =1:6 in volume) afforded the title compound as a light yellow oil (332 mg).

後処理

  1. stirringThe reaction mixture was then stirred for 21 hours
  2. customThe solvent was removed in vacuo
  3. extractionthe remaining residue was extracted with ethyl acetate/water (10 ml of each)
  4. customThe aqueous phase was separated
  5. extractionextracted twice with equal volumes of fresh ethyl acetate
  6. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-29704d8459b44dcaace328bcfd3d05c9
出典データセット
uspto-grants-1999_10
特許番号
US05968944

反応ノート

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