Trifluoroacetic acid → HCID 86638090, compound

Participants

Reaction Conditions

Reaction Steps

Compound (5) (8.4 g, 27 mmol) was dissolved in anhydrous CH2Cl2 (58 ml) and 3-chloroperoxybenzoic acid (mCPBA) (12.3 g) was added in one portion. The suspension was cooled to 0° C., and trifluoroacetic acid (2.0 ml) was added dropwise over 5-10 min. The reaction flask was protected from light, and the mixture was stirred for 3-5 days at room temperature, poured onto water (100 ml), and neutralized with ammonium hydroxide solution. The layers were separated, and the aqueous layer was extracted with CH2Cl2 (60 ml). After purification on a silica gel column (n-hexane/EtOAc=2:1) the title compound was obtained as a yellow oil (6) (4.24 g, 48%). TLC Rf=0.5 (n-hexane/EtOAc=3:1). 1H NMR (300 MHz, CDCl3) (NMR, Varian Gemini): δ 7.20 (t, J=7 Hz, 1H, Aryl H), 7.01-6.93 (m, 2H, 2H, Aryl Ha), 4.75 (s, 2H, Ph-CH2—N), 4.33 (s, 2H, CO—CH2—), 3.90-3.82 (m, 2H, M—CH2—), 2.97-2.92 (m, 2H, Ph-CH2—). Fast Atom Bombardment Mass Spectrometry (FABMS) m/z: 322 (M+1) (C13H11NO3ClF3).

Provenance & Evidence