Hydrochloric Acid → HCID 67459992, compound

Participants

Reaction Steps

TEA (88.4 μL) was added to a solution of methyl 3-[(3S,5R)-5-(4-chlorophenyl)morpholin-3-yl]acrylate (89 mg), vinylacetic acid (40.4 μL), and bis(2-oxo-3-oxazolidinyl)phosphinic chloride (121 mg) in THF (4 mL) at room temperature. The reaction solution was stirred at room temperature for two hours. Then, a 1 N hydrochloric acid solution and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was sequentially washed with a 1 N sodium hydroxide solution and brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 52.8 mg of methyl 3-[(3S,5R)-4-(3-butenoyl)-5-(4-chlorophenyl)morpholin-3-yl]-(E)-acrylate and 35.1 mg of methyl 3-[(3S,5R)-4-(3-butenoyl)-5-(4-chlorophenyl)morpholin-3-yl]-(Z)-acrylate. The property values of the isomers are as follows.

Provenance & Evidence