Pyridine → HCID 88321781, compound

Participants

Reaction Steps

A solution of (±)ethyl 1-azabicyclo[3.2.1]oct-3-en-3-yl carboxylate (D6) (1.9 g, 10.5 mmole) in 5M hydrochloric acid (25 ml) was heated at 100° C. for 7h. The reaction was concentrated in vacuo and dried by co-distillation with toluene. The resulting brown solid (2.0 g) was suspended in thionyl chloride (20 ml) and heated under reflux until all the acid had dissolved (approx. 10 minutes). After concentrating the reaction in vacuo, residual traces of volatile material were removed by co-distillation with toluene, and the residue was finally dried under high vacuum. A suspension of the acid chloride in absolute chloroform (50 ml) was treated with N,O-dimethylhydroxylamine hydrochloride (1.13 g, 11.5 mmole) and cooled in an ice-salt bath. Pyridine (4.2 ml, 5.3 mmole) was added dropwise with good stirring over a period of 1h. The reaction was allowed to warm to room temperature and stirred overnight. After cooling in an ice bath, the reaction was quenched with a saturated aqueous solution of potassium carbonate (25 ml). The aqueous layer was extracted with chloroform (3×25 ml), and the combined organic extracts were dried (Na2SO4) and concentrated in vacuo to give an oil which was extracted into ether, and then distilled on a kugelrohr (175° C./0.2 mmHg) to afford the title compound (D8) as a pale yellow oil (1.1 g, 54%) which solidified on cooling.

Provenance & Evidence