反应详情

N-allylpropane-1-sulfonamide (0.238 g, 1.456 mmol) is added to a solution of 9-borabicyclo[3.3.1]nonane (0.185 g, 1.519 mmol) in tetrahydrofuran (4 mL). The reaction mixture was stirred for 2 h at room temperature. (7R,8S)-8-(3-chlorobenzyl)-7-(pyrrolidin-1-yl)-5,6,7,8-tetrahydronaphthalen-2-yl trifluoromethanesulfonate (0.3 g, 0.633 mmol) dissolved in tetrahydrofuran (2 mL), sodium hydroxide (0.063 g, 1.582 mmol in 0.06 mL water) and palladium tetrakistriphenylphosphine (0.073 g, 0.063 mmol) were added. The reaction mixture was heated under reflux over night. The reaction mixture was diluted with ethyl acetate and washed with 1 M sodium hydroxide solution. The aqueous phase was extracted two more times with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and the solvent was evaporated in vacuo. The crude product was purified by preparative thin-layer-chromatography (silica gel, dichloromethane, methanol). The product was dissolved in dichloromethane. Excess 5N hydrochloric acid in ethanol was added. The solvent was evaporated and the product dried in vacuo. Yield: 53 mg (0.108 mmol, 17%).

1. temperatureThe reaction mixture was heated
2. temperatureunder reflux over night
3. washwashed with 1 M sodium hydroxide solution
4. extractionThe aqueous phase was extracted two more times with ethyl acetate
5. washThe combined organic extracts were washed with brine
6. dry with materialdried (MgSO4)
7. customthe solvent was evaporated in vacuo
8. customThe crude product was purified by preparative thin-layer-chromatography (silica gel, dichloromethane, methanol)
9. dissolutionThe product was dissolved in dichloromethane
10. additionExcess 5N hydrochloric acid in ethanol was added
11. customThe solvent was evaporated
12. customthe product dried in vacuo