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

HRID 1890749

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

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

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

Sources & evidence

ORD record: ord-978128e09c794bfa95ffcd1d26089dfe
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507491B2

Linked notes

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