p-Toluenesulphonyl cyanide → 8-Oxospiro[4.5]decane-7-carbonitrile

Temperature

-78 °C

LDA (1.83 mL, 3.66 mmol, 2.0 M in hexanes) was combined with THF (3.2 mL) and cooled to −78° C. To this mixture was added a solution of spiro[4.5]decan-8-one (0.50 g, 3.3 mmol) in THF (3.2 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 (0.59 g, 3.3 mmol) in THF (3.2 mL) at −78° C. The reaction mixture was allowed to stir at −78° C. for 45 mins then quenched with 0.5M 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. The residue was carried forward without further purification.

1. customthen taken up in a syringe
2. stirringto stir at −78° C. for 45 mins
3. customthen quenched with 0.5M NaOH
4. extractionextracted with EtOAc (2×)
5. washThe combined organic extracts were washed with 1N aqueous HCl, brine
6. dry with materialdried over anhydrous Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe crude residue was purified by MPLC on silica gel (
10. washa gradient elution of 0-50% EtOAc/hexanes)
11. concentrationconcentrated in vacuo

ORD record

ord-b2522bd082f24ec79461117fe80458d7

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962608B2