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Potassium vinyltrifluoroborate → 1-tert-butyl 2-methyl (2S,4R)-4-[(7-methoxy-2-oxo-6-vinyl-1,2-dihydroquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate

HRID 2045708
ノート
印刷プレビュー

反応式

HRID 2045708 の反応式
[CH:1]([B-](F)(F)F)=[CH2:2].[K+].Br[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[NH:15][C:14](=[O:21])[CH:13]=[C:12]2[O:22][C@H:23]1[CH2:27][N:26]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@H:25]([C:35]([O:37][CH3:38])=[O:36])[CH2:24]1>CCO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:20][O:19][C:18]1[CH:17]=[C:16]2[C:11]([C:12]([O:22][C@H:23]3[CH2:27][N:26]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@H:25]([C:35]([O:37][CH3:38])=[O:36])[CH2:24]3)=[CH:13][C:14](=[O:21])[NH:15]2)=[CH:10][C:9]=1[CH:1]=[CH2:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 23679353Potassium vinyltrifluoroborateHCID 59279885HCID 59279885、化合物

生成物 1

HCID 592799081-tert-butyl 2-methyl (2S,4R)-4-[(7-methoxy-2-oxo-6-vinyl-1,2-dihydroquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate収率 99.1%

試薬・触媒・溶媒 2

HCID 178418807HCID 178418807、化合物触媒HCID 702
Ethanol
溶媒

実験手順

Potassium vinyltrifluoroborate (0.913 g, 6.82 mmol), TEA (0.950 mL, 6.82 mmol), and PdCl2(dppf)-CH2Cl2 adduct (0.186 g, 0.227 mmol) were added to a solution of the product from step 2 (2.26 g, 4.54 mmol) in EtOH (45.4 mL). The mixture was then heated to reflux for 1 h. The EtOH was removed in vacuo, and the residue was taken up in EtOAc and extracted with water. The organic layer was dried over MgSO4, and the solvent was removed in vacuo. The crude material was purified on silica gradient elution, 0-5% MeOH/DCM) to yield 2.0 g (99%) of the title compound. LRMS ESI+ ((M-Boc)+H)+345.3.

後処理

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 1 h
  3. customThe EtOH was removed in vacuo
  4. extractionextracted with water
  5. dry with materialThe organic layer was dried over MgSO4
  6. customthe solvent was removed in vacuo
  7. customThe crude material was purified on silica gradient elution, 0-5% MeOH/DCM)

出典と根拠

ORDレコード
ord-f93848d647e94569bf633da037048bff
出典データセット
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08591878B2

反応ノート

読み込み中…

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