Cesium carbonate → 6-(2,2-Dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline

HRID 257069

반응식

HRID 257069 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH2:6][CH2:5]2.[I-].[Cs+].[CH3:15][O:16][CH:17]([O:20][CH3:21])[CH2:18]Br.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.[Cl-].[Na+].O>[CH3:15][O:16][CH:17]([O:20][CH3:21])[CH2:18][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH2:6][CH2:5]2

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 24601Cesium iodideHCID 816722-Bromo-1,1-dimethoxyethaneHCID 159083146-Hydroxy-1,2,3,4-tetrahydroisoquinolin-1-one

생성물 1

HCID 189638836-(2,2-Dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of 6-hydroxy-1-oxo-1,2,3,4-tetrahydroisoquinoline (25 g, 15.3 mmol), CsI (4 g, 15.3 mmol) and bromoacetaldehyde dimethyl acetal (40 ml, 338 mmol) in DMF (600 ml) is added Cs2CO3 (137.5 g, 460 mmol). The reaction mixture is heated at 60° overnight. After this time, the reaction is poured into 1 liter brine and the resulting suspension is extracted with EtOAc (4×400 ml). The combined EtOAc extracts are dried over MgSO4 and concentrated in vacuo. The residue is washed with Et2O to yield 6-(2,2-dimethoxyethoxy)-1-oxo-1,2,3,4-tetrahydroisoquinoline as a crystalline solid.

후처리

  1. temperatureThe reaction mixture is heated at 60° overnight
  2. extractionthe resulting suspension is extracted with EtOAc (4×400 ml)
  3. dry with materialThe combined EtOAc extracts are dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. washThe residue is washed with Et2O

출처 및 근거

ORD 기록
ord-1742ff794edb415bb609e30f4ecef1d1
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05260316

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