Phosphorus oxychloride → HCID 69827775, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (3aR,4S,6R,6aR)-6-methoxy-2,2-dimethyl-N-(2-oxobutyl)tetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide (740 mg) in dry toluene (10 ml), under nitrogen was added phosphorous oxychloride (1.44 ml) and the mixture was heated under reflux for 3.5 h. The reaction mixture was cooled to 0° C., quenched with saturated aqueous sodium bicarbonate (30 mls), stirred vigorously for 30 min and extracted with ethyl acetate (4×50 ml); the organic layers were combined, washed with brine (30 ml), dried (MgSO4) and concentrated in vacuo to give a crude product, which was purified by flash column chromatography on silica gel, eluting with a mixture of 5:1 to 7:2 cyclohexane:ethyl acetate, to give the title compound as a yellow oil (0.83 g).

Provenance & Evidence