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Triethylamine → (2R,4R)-2-[2-Fluoro-4-(2-oxo-piperidin-1-yl)-phenylcarbamoyl]-4-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 2217571
ノート
印刷プレビュー

反応式

HRID 2217571 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][CH3:14])[CH2:10][C@@H:9]1[C:15]([OH:17])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][C:26]2=[O:31])=[CH:21][C:20]=1[F:32].CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1.C(N(CC)CC)C>C(Cl)(Cl)Cl.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][CH3:14])[CH2:10][C@@H:9]1[C:15](=[O:17])[NH:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][C:26]2=[O:31])=[CH:21][C:20]=1[F:32])=[O:7])([CH3:2])([CH3:3])[CH3:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471TriethylamineHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 11459222(2R,4R)-1-[(tert-butoxy)carbonyl]-4-methoxypyrrolidine-2-carboxylic acidHCID 117890101-(4-Amino-3-fluoro-phenyl)-piperidin-2-one

生成物 1

HCID 11154790(2R,4R)-2-[2-Fluoro-4-(2-oxo-piperidin-1-yl)-phenylcarbamoyl]-4-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Into a solution of 6 (0.250 g, 1.02 mmol) in CHCl3 (10 mL) was added 7 (0.212 g, 1.02 mmol), EEDQ (0.302 g, 1.22 mmol), and triethylamine (0.213 mL, 1.53 mmol). The solution was stirred at reflux for 19 h before cooling to RT and adding EtOAc. The solution was washed sequentially with 10% aq. citric acid, 1N NaOH, water, and brine, before drying over MgSO4 and concentrating under reduced pressure. The crude material was purified by flash chromatography to reveal 8 (0.329 g, 74%) as a tan foam. MS: APCI (AP+): 436.1 (M)+, (AP−): 434.1 (M)−.

後処理

  1. temperatureat reflux for 19 h
  2. washThe solution was washed sequentially with 10% aq. citric acid, 1N NaOH, water, and brine
  3. dry with materialbefore drying over MgSO4
  4. concentrationconcentrating under reduced pressure
  5. customThe crude material was purified by flash chromatography

出典と根拠

ORDレコード
ord-967cfc370c5f42eba473cbd87d090ca6
出典データセット
uspto-grants-2008_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07407974B2

反応ノート

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