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

HRID 1890749

反応式

HRID 1890749 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-978128e09c794bfa95ffcd1d26089dfe
出典データセット
uspto-grants-2013_08
特許番号
US08507491B2

関連ノート

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