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 1740104노트

반응식

HRID 1740104 반응식
[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

참가 물질

5

반응물 3

HCID 6340IodoethaneHCID 24758Sodium hydride3회HCID 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

생성물 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-isoquinoline수율 141.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-29704d8459b44dcaace328bcfd3d05c9
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05968944

반응 노트

불러오는 중…