Trifluoroacetic acid → HCID 59323300, compound

Participants

Reaction Steps

427 mg of 1-[2-(tert-butoxycarbonylaminomethyl)-6-chlorophenyl]-3-phenyl-2-propanone was dissolved in 5 mL of methylene chloride, and 3 mL of trifluoroacetic acid was added thereto under ice-cooling, followed by stirring at room temperature for 1 hour. After confirming the loss of the starting material, it was concentrated under reduced pressure, and the residue obtained was dissolved in 5 mL of ethanol. 173 mg of sodium borohydride was added thereto under ice-cooling, followed by stirring at room temperature for 1 hour. After completion of the reaction, a saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue obtained was recrystallized using chloroform hexane to obtain 173 mg of a title compound as a white crystal. Further, a mother liquor upon recrystallization operation was purified using PLC (chloroform:methanol=20:1) to obtain 88.6 mg of a title compound as a pale yellow oily substance. In total, 262 mg (yield 89%) of a title compound was obtained.

Provenance & Evidence