Water → 2-Benzyl-1-(1-methoxy-1-methylethyl)-1,2,3,4-tetrahydroisoquinoline

HRID 2383048노트

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HRID 2383048 반응식
[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1[C:18]([OH:21])([CH3:20])[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:24]I.O>C1COCC1>[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1[C:18]([O:21][CH3:24])([CH3:19])[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6328Methyl iodide2회HCID 24758Sodium hydride2회HCID 59396310HCID 59396310, 화합물

생성물 1

HCID 593964802-Benzyl-1-(1-methoxy-1-methylethyl)-1,2,3,4-tetrahydroisoquinoline

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

With cooling in an ice-MeOH bath under an argon atmosphere, a solution of 2-(2-benzyl-1,2,3,4-tetrahydroisoquinolin-1-yl)propan-2-ol (1.27 g) in THF (7 mL) was added dropwise to a solution of sodium hydride (60%, 199 mg) in THF (5 mL), followed by stirring at room temperature for 0.5 hours. Then, the reaction liquid was cooled in ice and methyl iodide (0.42 mL) was added thereto. The mixture was stirred at room temperature for 8 hours. To the mixture were added sodium hydride (60%, 199 mg) and methyl iodide (0.42 mL), followed by stirring at room temperature for 12 hours. Water was added to the reaction solution, followed by extraction with EtOAc. The extract was washed with saturated brine, dried over magnesium sulfate, filtered, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-EtOAc) to obtain 2-benzyl-1-(1-methoxy-1-methylethyl)-1,2,3,4-tetrahydroisoquinoline (1.17 g).

후처리

  1. temperatureWith cooling in an ice-MeOH bath under an argon atmosphere
  2. customThen, the reaction liquid
  3. temperaturewas cooled in ice
  4. stirringThe mixture was stirred at room temperature for 8 hours
  5. stirringby stirring at room temperature for 12 hours
  6. extractionfollowed by extraction with EtOAc
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe resulting residue was purified by silica gel column chromatography (hexane-EtOAc)

출처 및 근거

ORD 기록
ord-563ff6488297451cab78b1d54f2fd8e0
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263607B2

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