Sodium Bicarbonate → 2-Fluoro-6-cinnamylbenzylamine

Participants

Reaction Steps

34 mg of t-butyl N-(2-fluoro-6-cinnamylbenzyl)carbamate was dissolved in a 4N hydrochloric acid/ethyl acetate solution, followed by stirring at room temperature for 1 hour. After completion of the reaction, to the reaction liquid was added an aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate, and the organic layer was then washed with an aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 24 mg of a crude composition of 2-fluoro-6-cinnamylbenzylamine as a light yellow oily substance. The obtained crude composition, 19 mg of 2-methoxycarbonylethylsulfonylchloride, and 21 mg of sodium carbonate were dissolved in 1 mL of methylene chloride and 1 mL of water, followed by stirring under ice-cooling for 1 hour. After completion of the reaction, water was added to the reaction liquid, followed by extraction with chloroform. The organic layer was then washed with an aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue obtained was purified using PLC (n-hexane:ethyl acetate=2:1) to obtain 29 mg (yield 79%) of a title compound as a yellow solid.

Provenance & Evidence