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

反応式

HRID 48850 の反応式
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]

参加物

9

反応物 4

HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 2734700Tert-butyl 2,2,2-trichloroethanimidate2 回HCID 227427542-[1-(3,4-dimethoxy-benzyl)-7-hydroxy-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl]-N-benzyl-acetamide

生成物 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-acetamide収率 75.5%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回HCID 8078Cyclohexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-940fa4589911448486d2b30bb65761f7
出典データセット
uspto-grants-2004_03
特許番号
US06703392B2

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