反应详情

A solution of 4-vinyl-piperidine-1-carboxylic acid tert-butyl ester (WO 9620192) (1.2 mM: 252 mg) in dry tetrahydrofuran (4 ml) was treated with a 0.5M solution of 9-borabicyclo[3.3.1]-nonane in tetrahydrofuran (1.2 mM; 2.4 ml) and stirred at room temperature for 6 hours under argon. The mixture was treated with the product of Example 100 (1.0 mM; 309 mg), 1,1′-bis(diphenylphosphino)ferrocene dichloro palladium(II) complex with dichloromethane (25 mg) and a 3M aqueous solution of sodium hydroxide (1 ml). The resulting mixture was heated at reflux under argon for 18 hours and purified on a 5 g SCX ion exchange cartridge. After removal of the solvent in vacuo the resulting yellow gum was treated with trifluoroacetic acid at room temperature for 2 hours and the solution passed through a 5 g SCX ion exchange cartridge. The solvent was removed in vacuo and the residue purified on a 5 g silica solid phase extraction cartridge eluting with 1-5-94 ammonia-methanol-dichloromethane to give the title compound as a white solid (23 mg). MS (ES+) m/e 342 [M+H]+.

1. temperatureThe resulting mixture was heated
2. temperatureat reflux under argon for 18 hours
3. custompurified on a 5 g SCX ion exchange cartridge
4. customAfter removal of the solvent in vacuo the resulting yellow gum
5. additionwas treated with trifluoroacetic acid at room temperature for 2 hours
6. customThe solvent was removed in vacuo
7. customthe residue purified on a 5 g silica solid phase extraction cartridge
8. washeluting with 1-5-94 ammonia-methanol-dichloromethane