Ammonium formate → 3-(Naphth-2-yl)-8-ethoxycarbonyl-8-azabicyclo[3.2.1]octane

HRID 1871912노트

반응식

HRID 1871912 반응식
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[CH2:17][CH:16]2[N:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:13]([CH2:14][CH2:15]2)[CH:12]=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]1[CH2:17][CH:16]2[N:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:13]([CH2:14][CH2:15]2)[CH2:12]1

참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 186899033-(Naphth-2-yl)-8-ethoxycarbonyl-8-azabicyclo[3.2.1]oct-2-ene

생성물 1

HCID 186899083-(Naphth-2-yl)-8-ethoxycarbonyl-8-azabicyclo[3.2.1]octane수율 70.4%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A mixture of 4.0 gm (13.0 mMol) 3-(naphth-2-yl)-8-ethoxycarbonyl-8-azabicyclo[3.2.1]oct-2-ene, 0.5 gm 10% palladium on carbon and 8.22 gm (130 mMol) ammonium formate in 100 mL ethanol was stirred at room temperature for 16 hours and then at reflux for 1.5 hours. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. The residue was subjected to silica gel chromatography. Fractions containing product were combined and concentrated under reduced pressure to provide 2.83 gm (70.4%) of 3-(naphth-2-yl)-8-ethoxycarbonyl-8-azabicyclo-[3.2.1]octane.

후처리

  1. temperatureat reflux for 1.5 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate concentrated under reduced pressure
  4. additionFractions containing product
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6b8e2e1765794a08b3cfb2001f8c34f4
출처 데이터셋
uspto-grants-2000_08
특허 번호
US06107307

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