Tetrahydrofuran → 4-Azatricyclo[2.2.1.0~2,6~]heptane-1-carbaldehyde

1-Cyano-4-azatricyclo[2.2.1.02,6 ]heptane (WO92/11261) (5.0 g, 42 mmol) in dry THF (150 ml) was treated with diisobutylaluminium hydride (84 ml of a 1M solution in hexane, 84 mmol) at 0° C. under nitrogen. After 3H the reaction mixture was allowed to warm to room temperature and quenched with 4N HCl. The THF was removed by concentrating in vacuo and the residue extracted with ethyl acetate (2×-discarded). The aqueous phase was made basic (pH 10-11) with potassium carbonate and the mixture extracted with dichloromethane (6×). The dichloromethane extracts were dried (MgSO4) and filtered. Evaporation of the solvent gave 2.8 g (55%) of the title compound.

1. customquenched with 4N HCl
2. customThe THF was removed
3. concentrationby concentrating in vacuo
4. extractionthe residue extracted with ethyl acetate (2×-discarded)
5. extractionthe mixture extracted with dichloromethane (6×)
6. dry with materialThe dichloromethane extracts were dried (MgSO4)
7. filtrationfiltered
8. customEvaporation of the solvent

ORD record

ord-b46a7c6fbddd4527b14914a984246bca

Source dataset

uspto-grants-1999_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05914338