Potassium Carbonate → HCID 42625857, compound

Temperature

85 °C

To a suspension of 1-azabicyclo[2.2.1]hept-4-yl(diphenyl)methanol (0.906 g, 3.24 mmol) in 1,2-dichloroethane (48 mL) was added AlCl3 (2.028 g, 15.3 mmol). The reaction was allowed to stir for 10 nm in and then TMSCN (2.04 mL, 15.3 mmol) was added. The reaction was sealed and heated to 85° C. for overnight. The reaction mixture was poured into a separatory funnel containing K2CO3 (aq satd) (200 mL) and EtOAc (200 mL). Extraction with EtOAc (3×200 mL) was performed. The combined organics were dried over MgSO4, filtered and concentrated under vacuum. The residue was dissolved in DMSO and purified by Gilson preparatory HPLC (w/0.1% TFA). The combined fractions were concentrated down under vacuum to remove the CH3CN. The resulting water layer was basified to pH=12 with 5N NaOH, and then extracted with EtOAc (3×150 mL). The combined fractions were dried over MgSO4, filtered, and concentrated under vacuum to give the title compound (0.53 g, 56.7%). EI-MS m/z 289 (M-H)+Rt (1.43 min).

1. additionwas added
2. customThe reaction was sealed
3. additionThe reaction mixture was poured into a separatory funnel
4. extractionExtraction with EtOAc (3×200 mL)
5. dry with materialThe combined organics were dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated under vacuum
8. dissolutionThe residue was dissolved in DMSO
9. custompurified by Gilson preparatory HPLC (w/0.1% TFA)
10. concentrationThe combined fractions were concentrated down under vacuum
11. customto remove the CH3CN
12. extractionextracted with EtOAc (3×150 mL)
13. dry with materialThe combined fractions were dried over MgSO4
14. filtrationfiltered
15. concentrationconcentrated under vacuum

ORD record

ord-cc4535f662f640c5bc47362c1741afa2

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07767691B2