Sodium hydride → (4aS,7aR)-1-(5-Phenylethynyl-pyridin-2-yl)-hexahydro-cyclopenta[d][1,3]oxazin-2-one

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Reaction Steps

In a 10 ml Round bottomed flask were dissolved (4aS,7aR)-hexahydro-cyclopenta[d]-[1,3]oxazin-2-one (80 mg, 0.57 mmol, 1.0 equiv.) and 2-fluoro-5-(phenylethynyl)pyridine (112 mg, 0.57 mmol, 1.0 equiv.) in 2 ml of DMF. Sodium hydride (60% suspension) (29.5 mg, 0.74 mmol, 1.3 equiv.) were added and the brown suspension was stirred at room temperature overnight. The reaction mixture was quenched with water and extracted twice with ethyl acetate. The combined organic phases were dried, filtered and concentrated. The crude material was purified by flash chromatography over a prepacked silica column eluting with 0-50% ethyl acetate in heptane gradient to yield 42.5 mg of the title compound as colorless amorphous solid, MS: m/e=319.1 (M+H+).

Provenance & Evidence