반응 #162315

반응 방정식

t-butyl 4-(4-fluoro-3-(trifluoromethylsulfonyloxy)phenyl)piperazine-1-carboxylate

(IR)-1-(2,4-dichlorophenyl)ethanamine

tBuDavePhos

Cs2CO3

→

(R)-t-butyl 4-(3-(1-(2,4-dichlorophenyl)ethylamino)-4-fluorophenyl)piperazine-1-carboxylate

용매

triethylamine

반응 조건

후처리

1. 1
   기타was purged with nitrogen for 3 min
2. 2
   기타the mixture was purged with nitrogen for 1 min
3. 3
   온도After cooling to room temperature
4. 4
   여과the suspension was filtered through a plug of Celite
5. 5
   세척washed with ethyl acetate (25 mL)
6. 6
   농축The filtrate was concentrated in vacuo
7. 7
   기타the resulting residue purified by flash chromatography (SiO2, 10-50% ethyl acetate in hexanes)

실험 절차

To a mixture of t-butyl 4-(4-fluoro-3-(trifluoromethylsulfonyloxy)phenyl)piperazine-1-carboxylate (0.50 g, 1.17 mmol) and (IR)-1-(2,4-dichlorophenyl)ethanamine (0.58 g, 3.05 mmol), tBuDavePhos (0.025 g, 0.070 mmol), and Cs2CO3 (0.80 g, 2.44 mmol) in triethylamine (3 mL) was purged with nitrogen for 3 min. Addition of Pd2(dba)3 (0.034 g, 0.037 mmol) was followed, and the mixture was purged with nitrogen for 1 min. The resulting mixture was heated at 100° C. under nitrogen for 4 h. After cooling to room temperature, the suspension was filtered through a plug of Celite, and washed with ethyl acetate (25 mL). The filtrate was concentrated in vacuo and the resulting residue purified by flash chromatography (SiO2, 10-50% ethyl acetate in hexanes) to afford (R)-t-butyl 4-(3-(1-(2,4-dichlorophenyl)ethylamino)-4-fluorophenyl)piperazine-1-carboxylate (0.36 g, 42.9 mmol, 62%).

출처