Norbornadiene → HCID 90303209, compound

Bicyclo[2.2.1]hepta-2,5-diene (0.84 g, 9.14 mmol), followed by Gd(OTf)3 (1.84 g, 3.05 mmol), 2-cyclopenten-1-one (5.00 g, 60.9 mmol) and TMS-CN (9.25 g, 91.4 mmol) were added to a degassed solution of Ni(cod)2 (0.84 g, 3.04 mmol) in THF (160 mL) and the mixture was stirred at RT for 4 h. Subsequently, the mixture was quenched with solid NaHCO3 and aq. sat. NaHCO3 and extracted with EtOAc. The comb. org. layers were washed with brine, dried over MgSO4 and conc. in vacuo. The residue, a yellow oil, was dissolved in THF/H2O (450 mL, 9:1). At 0° C., NBS (11.98 g, 67.3 mmol) was added and the mixture was stirred at 0° C. for 30 min. Subsequently, the mixture was quenched with aq. sat. Na2SO3 and extracted with EtOAc. The comb. org. layers were washed with aq. 5% NaHCO3 and brine, dried over Na2SO4, and conc. in vacuo. The residue was re-dissolved in EtOAc, washed multiple times with aq. 5% NaHCO3 and brine, the combined org. layer were dried over Na2SO4, and conc. in vacuo to provide a brown liquid.

1. customSubsequently, the mixture was quenched with solid NaHCO3 and aq. sat. NaHCO3
2. extractionextracted with EtOAc
3. washlayers were washed with brine
4. dry with materialdried over MgSO4 and conc. in vacuo
5. dissolutionThe residue, a yellow oil, was dissolved in THF/H2O (450 mL, 9:1)
6. stirringthe mixture was stirred at 0° C. for 30 min
7. customSubsequently, the mixture was quenched with aq. sat. Na2SO3
8. extractionextracted with EtOAc
9. washlayers were washed with aq. 5% NaHCO3 and brine
10. dry with materialdried over Na2SO4
11. dissolutionThe residue was re-dissolved in EtOAc
12. washwashed multiple times with aq. 5% NaHCO3 and brine
13. dry with materiallayer were dried over Na2SO4
14. customconc. in vacuo to provide a brown liquid

ORD record

ord-f02655b8c2eb47fc8ceb61cba0ae9374

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09388198B2