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乙烯三氟硼酸钾 → 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
笔记
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反应方程式

HRID 2045708 反应方程式
[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]
参与物实验过程后处理来源与证据反应笔记

参与物

5

反应物 2

HCID 23679353乙烯三氟硼酸钾HCID 59279885HCID 59279885,化合物

产物 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收率 99.1%

试剂、催化剂与溶剂 2

HCID 178418807HCID 178418807,化合物催化剂HCID 702乙醇溶剂

实验过程

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.

后处理

  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)

来源与证据

ORD记录
ord-f93848d647e94569bf633da037048bff
来源数据集
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
专利号
US08591878B2

反应笔记

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本页导航参与物实验过程后处理来源与证据反应笔记