3-Sulfolene → 5-Bromo-2-(1,1-dioxo-tetrahydro-thiophen-3-yl)-1,2,3,4-tetrahydro-isoquinoline

HRID 1890749

반응식

HRID 1890749 반응식
Cl.[Br:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][NH:7][CH2:8]2.[S:13]1([CH2:19][CH:18]=[CH:17][CH2:16]1)(=[O:15])=[O:14].[OH-].[K+]>O.C([O-])(O)=O.[Na+]>[Br:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][N:7]([CH:17]1[CH2:18][CH2:19][S:13](=[O:15])(=[O:14])[CH2:16]1)[CH2:8]2

참가 물질

6

반응물 3

HCID 64983-SulfoleneHCID 14797Potassium HydroxideHCID 450740035-Bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride

생성물 1

HCID 583178905-Bromo-2-(1,1-dioxo-tetrahydro-thiophen-3-yl)-1,2,3,4-tetrahydro-isoquinoline

시약·촉매·용매 2

HCID 962Water용매HCID 516892Sodium Bicarbonate용매

반응 조건

온도
70 °C

실험 절차

To a solution containing 5-bromo-1,2,3,4-tetrahydroisoquinoline hydrochloride (1.5 g, 6 mmol) and butadiene sulfone (1.2 g, 10.2 mmol) in water (20 mL) is added 1N KOH (10 mL). The reaction mixture is stirred at 70° C. for 24 hours. After cooling to ambient temperature, the reaction mixture is diluted with saturated NaHCO3 solution and extracted with dichloromethane three times. The organic phase is washed with brine and dried over Na2SO4 before drying by rotary evaporation. The crude product is purified by silica gel flash chromatography to afford 5-bromo-2-(1,1-dioxo-tetrahydro-thiophen-3-yl)-1,2,3,4-tetrahydro-isoquinoline as a wax-like solid. MS m/z 330.1 (M+1).

후처리

  1. temperatureAfter cooling to ambient temperature
  2. extractionextracted with dichloromethane three times
  3. washThe organic phase is washed with brine
  4. dry with materialdried over Na2SO4
  5. custombefore drying by rotary evaporation
  6. customThe crude product is purified by silica gel flash chromatography

출처 및 근거

ORD 기록
ord-978128e09c794bfa95ffcd1d26089dfe
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507491B2

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