반응 #975373

반응 방정식

4-bromo-4′-fluorobiphenyl

(R)-2-methylpiperazine

(+/−)-BINAP

sodium tert-butoxide

→

title product

(3R)-1-(4′-fluorobiphenyl-4-yl)-3-methylpiperazine

용매

toluene

반응 조건

후처리

1. 1
   기타was degassed 15 min under N2
2. 2
   온도The reaction was cooled to room temperature
3. 3
   여과filtered on a bed of cellite
4. 4
   세척washed with Et2O
5. 5
   세척The combined organic layers were then washed with H2O (3×)
6. 6
   건조dried over MgSO4
7. 7
   여과filtered
8. 8
   기타evaporated
9. 9
   기타to give a dark brown oil
10. 10
    기타This residue was purified by chromatography on silicagel (DCM/MeOH 20/80)

실험 절차

A mixture of (R)-2-methylpiperazine (2.2 g, 22.1 mmol, 1.0 eq.), tris(dibenzylidene acetone)dipalladium(0) (607 mg, 0.66 mmol, 0.03 eq.) and (+/−)-BINAP (137 mg, 0.22 mmol; 0.01 eq.) in toluene was degassed 15 min under N2. 4-bromo-4′-fluorobiphenyl (4.99 g, 19.9 mmol, 0.90 eq.) was added followed by sodium tert-butoxide (2.97 g, 30.9 mmol, 1.4 eq.). The resulting mixture was heated to 90° C. for 14 h. The reaction was cooled to room temperature, filtered on a bed of cellite and washed with Et2O. The combined organic layers were then washed with H2O (3×), dried over MgSO4, filtered and evaporated to give a dark brown oil. This residue was purified by chromatography on silicagel (DCM/MeOH 20/80) to give the title product as off white solid (3.0 g, 50%) M+(ESI): 271.3. HPLC (Condition A), Rt: 2.8 min (HPLC purity: 99.8%).

출처