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

HRID 1740115노트

반응식

HRID 1740115 반응식
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([N:14]2[C:18]([CH2:19][CH3:20])=[C:17]([CH2:21][N:22]3[C@@H:31]([CH2:32][O:33][CH2:34][CH3:35])[CH2:30][C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH2:23]3)[C:16]([CH2:36][CH3:37])=[N:15]2)=[C:9]([CH3:38])[CH:8]=1.O>O1CCCC1>[CH3:13][C:11]1[CH:12]=[CH:7][CH:8]=[C:9]([CH3:38])[C:10]=1[N:14]1[C:18]([CH2:19][CH3:20])=[C:17]([CH2:21][N:22]2[C@@H:31]([CH2:32][O:33][CH2:34][CH3:35])[CH2:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:23]2)[C:16]([CH2:36][CH3:37])=[N:15]1

참가 물질

5

반응물 3

HCID 962WaterHCID 53638919(R)-2-[1-(4-bromo-2,6-dimethylphenyl)-3,5-diethyl-1H-pyrazol-4-ylmethyl]-3-ethoxymethyl-1,2,3,4-tetrahydro-isoquinolineHCID 178418339Butyllithium

생성물 1

HCID 53917900(R)-2-[1-(2,6-Dimethylphenyl)-3,5-diethyl-1H-pyrazol-4-ylmethyl]-3-ethoxymethyl-1,2,3,4-tetrahydro-isoquinoline수율 60.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of n-butyl lithium (2.5 M hexane solution; 0.028 ml, 0.071 mmol) chilled to -78° C., a solution of (R)-2-[1-(4-bromo-2,6-dimethylphenyl)-3,5-diethyl-1H-pyrazol-4-ylmethyl]-3-ethoxymethyl-1,2,3,4-tetrahydro-isoquinoline (33 mg, 0.065 mmol) in anhydrous tetrahydrofuran (0.1 ml) was added dropwise. After stirring at -78° C. for 10 minutes, water (0.1 ml) was added. The resulting mixture was warmed to room temperature and stirred for 20 minutes. The reaction was quenched by addition of aqueous ammonium chloride (1 ml), and then extracted with ethyl acetate/water (5 ml of each). The separated organic extract was washed with an equal volume solution of aqueous ammonium chloride, dried over anhydrous sodium sulfate and concentrated in vacuo to afford a yellow oil (17 mg). Flash chromatography (silica gel, 40 micron mesh; elution with ethyl acetate/hexane=1:5 in volume) afforded the title compound (2 mg) as a yellow oil.

후처리

  1. temperatureThe resulting mixture was warmed to room temperature
  2. stirringstirred for 20 minutes
  3. customThe reaction was quenched by addition of aqueous ammonium chloride (1 ml)
  4. extractionextracted with ethyl acetate/water (5 ml of each)
  5. extractionThe separated organic extract
  6. washwas washed with an equal volume solution of aqueous ammonium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-3050971fb0c84c5ab82d638f0d6425b0
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05968944

반응 노트

불러오는 중…