反应详情

温度

-78 °C

BuLi (1.6M in hexane, 31.9 mL, 51.0 mmol) was added to a sol. of (4-bromo-phenoxy)-tert-butyl-dimethyl-silane (12.8 g, 44.5 mmol) in THF (150 mL) at −78° C. The mixture was stirred for 60 min at −78° C., and ZnCl2 (1.1M, 50.5 mL, 55.6 mmol) was added. The mixture was allowed to warm to rt, and a sol. of (rac.)-(1R*,5S*)-9-methyl-7-trifluoromethanesulfonyloxy-3,9-diaza-bicyclo[3.3.1]non-6-ene-3,6-dicarboxylic acid 3-tert-butyl ester 6-ethyl ester (WO 2003/093267; 17.0 g, 37.1 mmol) in THF (10 mL) and Pd(PPh3)4 (1.07 g, 0.927 mmol) were added. The mixture was stirred at 50° C. for 25 min, and was allowed to cool to rt. Aq. sat. NH4Cl was added, and the mixture was extracted with EtOAc (3×). The combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (EtOAc/heptane 6:4) yielded the title compound (15.9 g, 83%). LC-MS: tR=0.95 min, ES+: 517.25.

1. temperatureto warm to rt
2. stirringThe mixture was stirred at 50° C. for 25 min
3. temperatureto cool to rt
4. extractionthe mixture was extracted with EtOAc (3×)
5. dry with materialextracts were dried over Na2SO4
6. filtrationfiltered
7. customthe solvents were removed under reduced pressure
8. customPurification of the residue by FC (EtOAc/heptane 6:4)