Réaction #77128

Équation de réaction

tert.-butyl 2,2,2-trichloroacetimidate

NaHCO3

boron trifluoride diethyl etherate

tert.-butyl 2,2,2-trichloroacetimidate

2-[1-(3,4-dimethoxy-benzyl)-7-hydroxy-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl]-N-benzyl-acetamide

→

titled product

Rendement 75.5%

2-[1-(3,4-dimethoxy-benzyl)-7-(1-methyl-prop-2-oxy)-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl]-N-benzyl-acetamide

Rendement 75.5%

Solvants

ethyl acetate

water

dichloromethane

dichloromethane

cyclohexane

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwere added
2. 2
   Autrethe phases were separated
3. 3
   Extractionthe aqueous phase was extracted three times with ethyl acetate (30 mL)
4. 4
   ConcentrationThe combined organic phases were concentrated in vacuo
5. 5
   Autrepurified by flash-chromatography

Mode opératoire

At room temperature tert.-butyl 2,2,2-trichloroacetimidate (437 mg, 0.36 mL, 2.0 mmol) was added to a solution of 2-[1-(3,4-dimethoxy-benzyl)-7-hydroxy-6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl]-N-benzyl-acetamide (95.3 mg, 0.2 mmol) in dichloromethane (5.0 mL) and cyclohexane (5.0 mL). The reaction mixture was treated with a solution of boron trifluoride diethyl etherate (50 μL, 0.4 mmol) in 10 mL dichloromethane and stirred for 22 h. Another portion of tert.-butyl 2,2,2-trichloroacetimidate (244 mg, 0.20 mL, 1.1 mmol) was added. After stirring for three days a saturated solution of NaHCO3 (10 mL), water (10 mL) and ethyl acetate (40 mL) were added, the phases were separated and the aqueous phase was extracted three times with ethyl acetate (30 mL). The combined organic phases were concentrated in vacuo and purified by flash-chromatography to give the titled product (80.4 mg, 75%) as pale yellow oil.

Source