3-(3-Pyridyl)-2-carboethoxy-2-azabicyclo[2.2.2]oct-5-ene → HCID 53673921, 화합물

HRID 1870794노트

반응식

HRID 1870794 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH:12]3[CH2:13][CH2:14][CH:9]([CH:10]=[CH:11]3)[N:8]2[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:2]=1>C(O)(=O)C.[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH:12]3[CH2:11][CH2:10][CH:9]([CH2:14][CH2:13]3)[N:8]2[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:2]=1

참가 물질

4

반응물 1

HCID 186942083-(3-Pyridyl)-2-carboethoxy-2-azabicyclo[2.2.2]oct-5-ene

생성물 1

HCID 53673921HCID 53673921, 화합물수율 98%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 23938Palladium용매

실험 절차

A solution of the (+/-)-endo and (+/-)-exo isomers of 3-(3-pyridyl)-2-carboethoxy-2-azabicyclo[2.2.2]oct-5-ene, compound (II), (750 mg, 2.90 mmol) in glacial acetic acid (0.5 mL) and Pd/C (10%) was shaken under a H2 atmosphere in a Parr apparatus for 2 hours. The catalyst was removed by filtration over a bed of Celite and the filtrate was basified by addition of a solution of 40% of NaOH in water. The aqueous basic solution was extracted with dichloromethane (4×20 mL) to give 740 mg (98%) of compound (XII). 1H NMR (CDCl3): δ 8.48 (m, 2H), 7.60 (m, 2H), 4.78 and 4.67 (m, 1H), 4.30 (m, 1H), 4.13 and 4.10 (q, 2H), 2.19 (m, 2H), 1.90 (m, 3H), 1.63 (m, 4H), 1.28 and 0.90 (t, 3H).

후처리

  1. customThe catalyst was removed by filtration over a bed of Celite
  2. additionthe filtrate was basified by addition of a solution of 40% of NaOH in water
  3. extractionThe aqueous basic solution was extracted with dichloromethane (4×20 mL)

출처 및 근거

ORD 기록
ord-201c2c749555486e90a57cb85f86826b
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06100269

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