Trifluoroacetic acid → HCID 19605558, compound

Participants

Reaction Steps

6.8 g of 3-benzyl-1-(t-butoxycarbonylamino)-3-azabicyclo[3.2.0]heptane was dissolved in 20 ml of methylene chloride, and 50 ml of trifluoroacetic acid was added thereto, followed by stirring for 3 hours. The reaction mixture was concentrated, mixed with an aqueous solution of sodium hydroxide under cooling with ice, and extracted with chloroform. After the extract was dried over anhydrous magnesium sulfate, the chloroform was distilled off. The resulting crude product was dissolved in 47 ml of formic acid, and 17 g of acetic anhydride was added dropwise thereto, under cooling with ice, over a period of 90 minutes. After the addition of ice water, the resulting mixture was neutralized by the addition of an aqueous solution of sodium hydroxide under cooling with ice, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (using a 30:1 mixture of chloroform and methanol as the eluent) to obtain 3.1 g of 3-benzyl-1-formylamino-3-azabicyclo[3.2.0]heptane.

Provenance & Evidence