반응 #2392346

반응 방정식

3-(1-BOC-2-(S)-pyrrolidinylmethoxy)-5-bromopyridine

5,5-dimethyl-hexadiene

tri-o-tolylphosphine

NaHCO3

→

oil

수율 75.0%

3-(1-BOC-2-(S)-Pyrrolidinylmethoxy)-5-(5,5-Dimethyl-1,3-hexadienyl)pyridine

수율 75.0%

용매

acetonitrile

NEt3

반응 조건

후처리

1. 1
   온도After cooling to room temperature
2. 2
   추출The mixture was extracted with EtOAc (2×)
3. 3
   건조The combined organic layers were dried (MgSO4)
4. 4
   농축concentrated
5. 5
   기타chromatographed (silica gel; hexane/EtOAc, 5:1 to 2:1)

실험 절차

To a solution of 3-(1-BOC-2-(S)-pyrrolidinylmethoxy)-5-bromopyridine (500 mg, 1.40 mmol) in acetonitrile (15 mL) and NEt3 (3.2 mL) was added 5,5-dimethyl-hexadiene (0.5 g, 4.54 mmol), palladium acetate (35 mg, 0.16 mmol) and tri-o-tolylphosphine (175 mg). The reaction mixture was heated in a sealed tube at 100° C. for 16 h. After cooling to room temperature, saturated NaHCO3 was added. The mixture was extracted with EtOAc (2×). The combined organic layers were dried (MgSO4), concentrated and chromatographed (silica gel; hexane/EtOAc, 5:1 to 2:1) to afford an oil (403 mg, 75%): 1H NMR (CDCl3, 300 Hz) δ 1.48 (s, 9H), 1.82-1.92 (m, 2H), 2.00-2.08 (m, 2H), 3.30-3.50 (m, 2H), 3.90 (br, 1H), 4.08-4.26 (m, 2H), 5.93 (d, 1H, J=15.5 Hz), 6.15 (dd, 1H, J=10.0, 15.0 Hz), 6.42 (d, 1H, J=16.0 Hz), 6.90 (m, 1H), 8.12 (s, 2H), 8.20 (s, 1H); MS (CI/NH3) m/z 387 (M+H)+.

출처