反应详情

Add 9-BBN (0.5 M THF solution, 13.7 mL, 6.85 mmol) to a 100 mL schlenk flask containing (S)-1,4-bis(toluene-4-sulfonyl)-2-vinyl-piperazine(0.96 g, 2.3 mmol) in THF (5 mL), at room temperature under nitrogen and stir. After 18 hours, treat the reaction with tetrakis(triphenylphosphine) palladium (53 mg, 0.046 mmol), triphenyl phosphine (94.6 mg, 0.36 mmol), iodiobenzene (0.703 g, 3.4 mmol) and 3N NaOH (2.8 mL, 8.4 mmol) and heat to reflux. After 24 hours, cool the reaction to room temperature, remove in vacuo the THF solvent, dilute the residue with CH2Cl2, wash with 1N HCl, brine, and dry over Na2SO4. Purification by flash chromatography twice (Gradient: Hexanes/CH2Cl2=50/50, to Hexanes/CH2Cl2/EtOAc=40/40/10), and recrystallization in MeOH gives 860 mg (75%) of the title compound: mass spectrum (electrospray): (m/z)=499.2 (M+1); 1H NMR (CDCl3): δ7.58–7.54 (m, 4H), 7.33–7.20 (m, 7H), 7.19–7.07 (m, 2H), 3.99 (m, 1H), 3.81–3.78 (m, 1H), 3.64–3.60 (m, 2H), 3.22 (dt, 1H, J=3.2 Hz, J=12.4 Hz), 2.57–2.41 (m, 2H), 2.41 (s, 3H), 2.33 (s, 3H), 2.33–2.20 (m, 2H), 2.03–1.98 (m, 1H), 1.75–1.63 (m, 1H).

1. additiontreat
2. temperatureheat to reflux
3. waitAfter 24 hours
4. temperaturecool
5. customthe reaction to room temperature
6. customremove in vacuo the THF solvent
7. additiondilute the residue with CH2Cl2
8. washwash with 1N HCl, brine
9. dry with materialdry over Na2SO4
10. customPurification
11. customby flash chromatography twice (Gradient: Hexanes/CH2Cl2=50/50, to Hexanes/CH2Cl2/EtOAc=40/40/10), and recrystallization in MeOH