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

Participants

Reaction Steps

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.

Provenance & Evidence