Boron trifluoride etherate → 2-[1-(3,4-dimethoxy-benzyl)-7-(1-methyl-prop-2-oxy)-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl]-N-benzyl-acetamide

HRID 48850

반응식

HRID 48850 반응식
ClC(Cl)(Cl)C(=N)O[C:5]([CH3:8])([CH3:7])C.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:42]=[CH:43][C:44]=1[O:45][CH3:46])[CH2:17][CH:18]1[C:27]2[C:22](=[CH:23][C:24]([O:29][CH3:30])=[C:25]([OH:28])[CH:26]=2)[CH2:21][CH2:20][N:19]1[CH2:31][C:32]([NH:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33].B(F)(F)F.[CH3:51]COCC.C([O-])(O)=O.[Na+]>ClCCl.C1CCCCC1.C(OCC)(=O)C.O>[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:42]=[CH:43][C:44]=1[O:45][CH3:46])[CH2:17][CH:18]1[C:27]2[C:22](=[CH:23][C:24]([O:29][CH3:30])=[C:25]([O:28][CH:5]([CH3:7])[CH2:8][CH3:51])[CH:26]=2)[CH2:21][CH2:20][N:19]1[CH2:31][C:32]([NH:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33]

참가 물질

9

반응물 4

HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 2734700Tert-butyl 2,2,2-trichloroethanimidate2회HCID 227427542-[1-(3,4-dimethoxy-benzyl)-7-hydroxy-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl]-N-benzyl-acetamide

생성물 1

HCID 227427802-[1-(3,4-dimethoxy-benzyl)-7-(1-methyl-prop-2-oxy)-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl]-N-benzyl-acetamide수율 75.5%

시약·촉매·용매 4

HCID 962Water용매HCID 6344Dichloromethane용매2회HCID 8078Cyclohexane용매HCID 8857Ethyl Acetate용매

실험 절차

At room temperature tert.-butyl 2,2,2-trichloroacetimidate (437 mg, 0.36 mL, 2.0 mmol) was added to a solution of 2-[1-(3,4-dimethoxy-benzyl)-7-hydroxy-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl]-N-benzyl-acetamide (95.3 mg, 0.2 mmol) in dichloromethane (5.0 mL) and cyclohexane (5.0 mL). The reaction mixture was treated with a solution of boron trifluoride diethyl etherate (50 μL, 0.4 mmol) in 10 mL dichloromethane and stirred for 22 h. Another portion of tert.-butyl 2,2,2-trichloroacetimidate (244 mg, 0.20 mL, 1.1 mmol) was added. After stirring for three days a saturated solution of NaHCO3 (10 mL), water (10 mL) and ethyl acetate (40 mL) were added, the phases were separated and the aqueous phase was extracted three times with ethyl acetate (30 mL). The combined organic phases were concentrated in vacuo and purified by flash-chromatography to give the titled product (80.4 mg, 75%) as pale yellow oil.

후처리

  1. additionwere added
  2. customthe phases were separated
  3. extractionthe aqueous phase was extracted three times with ethyl acetate (30 mL)
  4. concentrationThe combined organic phases were concentrated in vacuo
  5. custompurified by flash-chromatography

출처 및 근거

ORD 기록
ord-940fa4589911448486d2b30bb65761f7
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703392B2

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