Sodium Methoxide → HCID 19809515, compound

Participants

Reaction Steps

A solution of (±)5-(2-chloromethyl-1,3-oxazol-5-yl)-1-azabicyclo[3.2.1]octane hydrochloride (D25) (75 mg, 0.28 mmole) in dry methanol (2 ml) was added dropwise over 2h to a solution of sodium methoxide in methanol (15 ml of a 25 wt % solution, 66 mmole), under nitrogen, cooled in ice. After evaporation of the solvent in vacuo the residue was treated with saturated aqueous potassium carbonate solution (10 ml) and extracted with chloroform. The combined extracts were dried over sodium sulphate then concentrated in vacuo. The residue was chromatographed on neutral alumina in a gradient of 0-0.5% methanol in chloroform. This afforded the title compound (E11) as an oil (50 mg, 79%) which was converted into the hydrochloride salt m.p. 129°-131° C. (from acetone-ether).

Provenance & Evidence