2-[[(8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepin-10yl)-carbonyl]amino]-N-methoxy-N-methylacetamide → 8-chloro-N-(2-oxo-3-butenyl)dibenz-[b,f][1,4]oxazepin-10(11H)-carboxamide

Participants

Reaction Steps

To a stirred solution of 2-[[(8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepin-10yl)-carbonyl]amino]-N-methoxy-N-methylacetamide (3.2 grams) in anhydrous tetrahydrofuran (35 mL) at -70° C. (dry ice/acetone bath) under a nitrogen atmosphere was added dropwise a solution of vinylmagnesium bromide (1.0M in tetrahydrofuran; 28 mi) in tetrahydrofuran (15 mL). The ice bath was removed, and the reaction was stirred to room temperature for one hour. The reaction was poured into 1M NaH2PO4 (250 mL) and extracted with ethyl acetate (3×200 mL). The combined ethyl acetate extracts were washed with 1M NaH2PO4 (2×250 mL) and brine (250 mL), dried over MgSO4, and evaporated in vacuo. The crude product was purified by flash chromatography through silica gel 60 (500 mL) using 9:1 methylene chloride:ethyl acetate to yield a colorless glass. The yield of the title compound was 2.25 grams (77%).

Provenance & Evidence