Ethanesulfonyl chloride → 2-(1-(Ethylsulfonyl)azetidin-3-ylidene)acetonitrile

tert-Butyl 3-(cyanomethylidene)azetidine-1-carboxylate (5.0 g, 26 mmol) was dissolved in 4M HCl in dioxane (25.7 mL) and allowed to stir at ambient temperature for 16 hours. The mixture was concentrated to dryness in vacuo, then dissolved in DCM (30.0 mL) and cooled to −10° C. DIPEA (11.6 g, 90.0 mmol) was added followed by ethanesulfonyl chloride (5.0 g, 39 mmol). The resulting mixture was allowed to stir for 7 hours before the mixture was diluted with water and extracted with DCM. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by MPLC on silica gel (using a gradient elution of 5-70% EtOAc/heptane). Desired fractions were identified, combined, and concentrated in vacuo to afford the title compound.

1. concentrationThe mixture was concentrated to dryness in vacuo
2. dissolutiondissolved in DCM (30.0 mL)
3. temperaturecooled to −10° C
4. stirringto stir for 7 hours before the mixture
5. extractionextracted with DCM
6. dry with materialThe organic layer was dried over anhydrous Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe residue was purified by MPLC on silica gel (
10. washa gradient elution of 5-70% EtOAc/heptane)
11. concentrationconcentrated in vacuo

ORD record

ord-a34d1429a63846edbd91b2896a60e687

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09328099B2