Nitric Acid → HCID 71184081, compound

Participants

Reaction Conditions

Reaction Steps

(1SR,7SR)-1-(2-Fluorophenyl)-4-thia-2-azabicyclo[5.1.0]oct-2-en-3-amine (intermediate A5a) (1.22 g, 5.16 mmol, Eq: 1.00) was dissolved in conc. sulfuric acid (20.3 g, 11.0 ml, 207 mmol, Eq: 40), then at 0° C. fuming nitric acid (488 mg, 321 μl, 7.74 mmol, Eq: 1.5) was added dropwise with an Eppendorf pipette. The light brown solution was stirred at 0° C. for 2 hours. The reaction mixture was poured on ice and basified with conc NaOH (pH=10) followed by the extraction with dichloromethane. The organic layer was separated, dried over Na2SO4, filtered and evaporated to dryness to give the (1SR,7SR)-1-(2-fluoro-5-nitrophenyl)-4-thia-2-azabicyclo[5.1.0]oct-2-en-3-amine (995 mg, 3.54 mmol, 68.5% yield). as a yellow solid. The crude product was used in the next step without further purification. MS (ISP): m/z=237.2 [(M+H)+].

Provenance & Evidence