Ammonium Chloride → (5R)-5-[(E)-2-(5-benzyl-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-one

HRID 70676ノート

反応式

HRID 70676 の反応式
[Br-].[CH2:2]([Zn+])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1.Br[C:27]1[CH:28]=[CH:29][C:30](/[C:35](/[C:43]2[CH:48]=[CH:47][C:46]([C:49]([CH3:52])([CH3:51])[CH3:50])=[CH:45][CH:44]=2)=[CH:36]/[C@@H:37]2[NH:41][C:40](=[O:42])[CH2:39][CH2:38]2)=[N:31][C:32]=1[O:33][CH3:34].[Cl-].[NH4+]>O1CCCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:2]([C:27]1[CH:28]=[CH:29][C:30](/[C:35](/[C:43]2[CH:44]=[CH:45][C:46]([C:49]([CH3:52])([CH3:51])[CH3:50])=[CH:47][CH:48]=2)=[CH:36]/[C@@H:37]2[NH:41][C:40](=[O:42])[CH2:39][CH2:38]2)=[N:31][C:32]=1[O:33][CH3:34])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 521585Tris(furan-2-yl)phosphaneHCID 58452636(5R)-5-[(E)-2-(5-bromo-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-oneHCID 178419772HCID 178419772、化合物

生成物 1

HCID 67397174(5R)-5-[(E)-2-(5-benzyl-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-one

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
110 °C

実験手順

0.05 M benzylzinc(II) bromide (385 μL), tris(dibenzylideneacetone)dipalladium(0) (8.0 mg) and tri(2-furyl)phosphine (15 mg) were added to a solution of (5R)-5-[(E)-2-(5-bromo-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-one obtained in Reference Example 4-42(2) (30 mg) in tetrahydrofuran (2 mL), and the mixture was stirred under microwave irradiation at 110° C. for one hour. An ammonium chloride solution was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→1:0) to give (5R)-5-[(E)-2-(5-benzyl-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-one (23 mg).

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→1:0)

出典と根拠

ORDレコード
ord-bfbfcc32e518474d9d9767bb8c3d6ad7
出典データセット
uspto-grants-2014_09
特許番号
US08822503B2

反応ノート

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