3-Sulfolene → HCID 58317890, compound

HRID 1505061

Reaction equation

HRID 1505061 reaction equation
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

Participants

6

Reactant 3

HCID 64983-SulfoleneHCID 14797Potassium HydroxideHCID 450740035-Bromo-1,2,3,4-tetrahydroisoquinoline--hydrogen chloride (1/1)

Product 1

HCID 58317890HCID 58317890, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
70 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-cdd90c8f2b364f749a8d1cffc121e02d
Source dataset
uspto-grants-2015_12
Patent number
US09216964B2

Linked notes

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