반응 #313639

반응 방정식

tert-butyl [(3R)-1-benzyl-3-pyrrolidinyl](6-chloro-2-pyrazinyl)carbamate

ethyl acrylate

tris(2-methylphenyl)phosphine

N,N-diisopropylethylamine

→

ethyl (2E)-3-(6-{[(3R)-1-benzyl-3-pyrrolidinyl](tert-butoxycarbonyl)amino}-2-pyrazinyl)acrylate

용매

DMF

water

반응 조건

후처리

1. 1
   온도to cool to ambient temperature
2. 2
   추출extracted with ethyl acetate
3. 3
   세척The organic phase was washed with brine
4. 4
   건조dried over Na2SO4
5. 5
   농축concentrated in vacuo
6. 6
   기타The residue was purified by silica gel column chromatography
7. 7
   세척eluting with a mixture of chloroform and methanol (96:4 v/v)

실험 절차

To a stirred solution of tert-butyl [(3R)-1-benzyl-3-pyrrolidinyl](6-chloro-2-pyrazinyl)carbamate (910 mg) in DMF (15 mL) was added ethyl acrylate (1.27 mL), palladium(II) acetate (26 mg), tris(2-methylphenyl)phosphine (107 mg), and N,N-diisopropylethylamine (1.22 mL). The mixture was stirred in the sealed tube at 150° C. for 3 days. The resulting mixture was allowed to cool to ambient temperature, poured into water, and extracted with ethyl acetate. The organic phase was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of chloroform and methanol (96:4 v/v) to give ethyl (2E)-3-(6-{[(3R)-1-benzyl-3-pyrrolidinyl](tert-butoxycarbonyl)amino}-2-pyrazinyl)acrylate (755 mg) as a pale yellow foam.

출처