Toluene → tert-Butyl 2-(pyrrolidin-1-ylmethyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate

HRID 2388681노트

반응식

HRID 2388681 반응식
C1(C)C=CC=CC=1.CS(O[CH2:13][C:14]1[S:22][C:21]2[CH2:20][CH2:19][N:18]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:17][C:16]=2[CH:15]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[NH:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1>C(OCC)(=O)C>[N:36]1([CH2:13][C:14]2[S:22][C:21]3[CH2:20][CH2:19][N:18]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:17][C:16]=3[CH:15]=2)[CH2:40][CH2:39][CH2:38][CH2:37]1

참가 물질

6

반응물 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 86635666tert-Butyl 2-((methylsulfonyloxy)methyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate

생성물 1

HCID 86635667tert-Butyl 2-(pyrrolidin-1-ylmethyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate수율 35%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
25 °C

실험 절차

To a toluene solution (30 ml) of tert-butyl 2-((methylsulfonyloxy)methyl)-6,7-dihydrothieno[3,2-c]pyridine-5(4H)-carboxylate (5.3 mmol) was added potassium carbonate (26.5 mmol) and pyrrolidine (6.36 mmol) and the resulting reaction mixture was refluxed for 16 h. It was cooled to 25° C., diluted with ethyl acetate and the organic layer was successively washed with water and brine. After drying over sodium sulfate, the organic layer was evaporated under reduced pressure to give the crude product which was purified by column chromatography (5% methanol in dichloromethane). Yield: 35%.

후처리

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 16 h
  3. washthe organic layer was successively washed with water and brine
  4. dry with materialAfter drying over sodium sulfate
  5. customthe organic layer was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-6983321746584767be6fecaa2b960c65
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268814B2

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