6-oxospiro[2.5]oct-7-ene-7-carbonitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6-Oxospiro[2.5]oct-4-ene-5-carbonitrile (0.16 g, 1.1 mmol) was dissolved in MeOH (11 mL) and combined with 10% palladium on activated carbon (0.12 g, 0.11 mmol). The resulting mixture was subjected to alternating vacuum and H2 gas (4×). The mixture was then stirred under an atmosphere of H2 (50 psi) for 16 hours. The mixture was then subjected to alternating vacuum and N2 gas (4×). The mixture was filtered through celite and rinsed with MeOH. The filtrate was concentrated in vacuo to afford the title compound. The material was used without further purification. The mixture was filtered through celite rinsed with MeOH The filtrate was concentrated in vacuo

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: LDA (1.34 mL, 2.69 mmol, 2.0 M in hexanes) was combined with THF (2.4 mL) and cooled to −78° C. To this mixture was added a solution of spiro[2.5]octan-6-one (0.30 g, 2.4 mmol) in THF (2.4 mL). The resulting mixture was stirred at −78° C. for 20 mins then taken up in a syringe and added to a mixture of tosyl cyanide (0.88 g, 4.8 mmol) in THF (2.4 mL) at −78° C. The reaction mixture was allowed to stir at −78° C. for 45 mins then quenched with 0.5 M NaOH and extracted with EtOAc (2×) The combined organic extracts were washed with 1N aqueous HCl, brine, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by MPLC on silica gel (using a gradient elution of 0-50% EtOAc/hexanes). Desired fractions were identified, combined and concentrated in vacuo to afford the title compound. then taken up in a syringe to stir at −78° C. for 45 mins then quenched with 0.5 M NaOH extracted with EtOAc (2×) The combined organic extracts were washed with 1N aqueous HCl, brine dried over anhydrous Na2SO4 filtered concentrated in vacuo The crude residue was purified by MPLC on silica gel ( a gradient elution of 0-50% EtOAc/hexanes) concentrated in vacuo