Hydrochloric Acid → HCID 11750834, compound

Participants

Reaction Steps

0.152 ml (2.2 equivalents) of 1,3-dimethylpropyleneurea and then 1.286 ml (2.2 equivalents) of 1.06M lithium bis(trimethylsilyl)amide in tetrahydrofuran are added at ambient temperature to 200 mg (0.58 mmol) of 1-[3-methylene-5-(phenylsulfonyl)-2,3,4,5-tetrahydro-1-benzoxepin-7-yl]ethanone, prepared according to example 13, in solution in 5.8 ml of tetrahydrofuran. The reaction medium then assumes a dark yellow color. After 15 minutes, 0.0698 ml (1 equivalent) of benzyl bromide is added. Water is immediately added, and 1N hydrochloric acid and dichloromethane. After separating the organic and aqueous phases, the aqueous phase is extracted 3 times with dichloromethane. The combined organic phases are washed with brine, are dried and are finally concentrated under vacuum. The crude reaction product is purified by chromatography on silica gel (ethyl acetate/heptane 30/70) to provide 245 mg (97%) of 1-[5-benzyl-3-methylene-5-(phenylsulfonyl)-2,3,4,5-tetrahydro-1-benzoxepin-7-yl]ethanone in the form of a white solid; M.p.=131–132° C.

Provenance & Evidence