Water → Pyrrolidine-1,2-dicarboxylic acid 2-{2-[9-(2-bromo-acetyl)-5,7-dihydro-dibenzo[c,e]oxepin-3-yl]-2-oxo-ethyl}ester 1-tert-butyl ester

HRID 417416

反応式

HRID 417416 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]([O:15][CH2:16][C:17]([C:19]1[CH:20]=[CH:21][C:22]2[C:28]3[CH:29]=[CH:30][C:31](Br)=[CH:32][C:27]=3[CH2:26][O:25][CH2:24][C:23]=2[CH:34]=1)=[O:18])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[CH:40]=[CH:41][O:42]CC)CCC.O.C1C(=O)N([Br:61])C(=O)C1>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]([O:15][CH2:16][C:17]([C:19]1[CH:20]=[CH:21][C:22]2[C:28]3[CH:29]=[CH:30][C:31]([C:41](=[O:42])[CH2:40][Br:61])=[CH:32][C:27]=3[CH2:26][O:25][CH2:24][C:23]=2[CH:34]=1)=[O:18])=[O:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 2763294(Z)-1-Ethoxy-2-(tributylstannyl)etheneHCID 66620516Pyrrolidine-1,2-dicarboxylic acid 2-[2-(9-bromo-5,7-dihydro-dibenzo[c,e]oxepin-3-yl)-2-oxo-ethyl]ester 1-tert-butyl ester

生成物 1

HCID 72337884Pyrrolidine-1,2-dicarboxylic acid 2-{2-[9-(2-bromo-acetyl)-5,7-dihydro-dibenzo[c,e]oxepin-3-yl]-2-oxo-ethyl}ester 1-tert-butyl ester収率 90.3%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

To the solution of pyrrolidine-1,2-dicarboxylic acid 2-[2-(9-bromo-5,7-dihydro-dibenzo[c,e]oxepin-3-yl)-2-oxo-ethyl]ester 1-tert-butyl ester (160 mg, 0.30) and tributyl(ethoxyvinyl)stannane (112 μl, 0.33 mmol) in dioxane (2 ml) was added PdCl2(PPh3)2 (8 mg). The mixture was heated at 80° C. for 16 hours and was cooled to 0° C. Water (0.7 ml) was added, followed by slow addition of NBS (59, 0.33 mmol) over 5 minutes period. The mixture was stirred at 0° C. for additional 40 minutes, and the solvent was removed under reduced pressure. The mixture was diluted with EtOAc, and was washed with water and brine and dried with sodium sulfate. Concentration and purification by flash column chromatography (hexane/EtOAc) gave pyrrolidine-1,2-dicarboxylic acid 2-{2-[9-(2-bromo-acetyl)-5,7-dihydro-dibenzo[c,e]oxepin-3-yl]-2-oxo-ethyl}ester 1-tert-butyl ester (156 mg). m/z: 593.9 (M+Na)+.

後処理

  1. temperaturewas cooled to 0° C
  2. customthe solvent was removed under reduced pressure
  3. additionThe mixture was diluted with EtOAc
  4. washwas washed with water and brine
  5. dry with materialdried with sodium sulfate
  6. concentrationConcentration and purification by flash column chromatography (hexane/EtOAc)

出典と根拠

ORDレコード
ord-97ceb9396a784715b56e09f029f6809e
出典データセット
uspto-grants-2012_01
特許番号
US08088368B2

関連ノート

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