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1-Bromo-2,4-difluorobenzene → (2S,4S)-1-Boc-4-[(2,4-difluorophenyl)amino]-2[(dimethylamino)carbonyl]pyrrolidine

HRID 1361335
ノート
印刷プレビュー

反応式

HRID 1361335 の反応式
[C:1]([N:8]1[CH2:12][C@@H:11]([NH2:13])[CH2:10][C@H:9]1[C:14]([N:16]([CH3:18])[CH3:17])=[O:15])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.Br[C:47]1[CH:52]=[CH:51][C:50]([F:53])=[CH:49][C:48]=1[F:54]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([N:8]1[CH2:12][C@@H:11]([NH:13][C:47]2[CH:52]=[CH:51][C:50]([F:53])=[CH:49][C:48]=2[F:54])[CH2:10][C@H:9]1[C:14]([N:16]([CH3:18])[CH3:17])=[O:15])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]
参加物反応条件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 676741-Bromo-2,4-difluorobenzeneHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 66971238tert-butyl (2S,4S)-4-amino-2-(dimethylcarbamoyl)pyrrolidine-1-carboxylate

生成物 1

HCID 66970978(2S,4S)-1-Boc-4-[(2,4-difluorophenyl)amino]-2[(dimethylamino)carbonyl]pyrrolidine収率 78%

試薬・触媒・溶媒

2
HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

To a solution of (2S,4S)-1-Boc-4-amino[(dimethylamino)carbonyl]pyrrolidine (8 g, 31.5 mmol) prepared in Step C in toluene (100 ml) was added sodium t-butoxide (3.46 g, 36 mmol), 2-(di-t-butylphosphino)biphenyl (800 mg, 2.68 mmol), tris(dibenzylideneacetone)dipalladium(0) (1.6 g, 1.79 mmol) and 1-bromo-2,4-difluorobenzene (6.94 g, 36 mmol), and the solution was stirred at 110° C. for 10 h. After the reaction finished, the solution was filtered through Celite, and extracted with water and EtOAc. The organic layer was dried over MgSO4, concentrated in vacuo, and purified by column chromatography (eluent, EtOAc/Hex=1/4) to give the title compound (1.5 g, 78%).

後処理

  1. filtrationthe solution was filtered through Celite
  2. extractionextracted with water and EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography (eluent, EtOAc/Hex=1/4)

出典と根拠

ORDレコード
ord-8d6fcdda243c4b369bf8a8141f9acf90
出典データセット
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07879852B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート