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

HRID 2388681ノート

反応式

HRID 2388681 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
25 °C

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-6983321746584767be6fecaa2b960c65
出典データセット
uspto-grants-2012_09
特許番号
US08268814B2

反応ノート

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