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Pyridine → (1S,2S)-2-[4-((R)-7-Fluoro-4-phenoxy-indan-1-yloxy)-phenyl]-cyclopropanecarboxylic acid

HRID 625712
ノート
印刷プレビュー

反応式

HRID 625712 の反応式
C([O:3][C:4]([C@H:6]1[CH2:8][C@@H:7]1[C:9]1[CH:14]=[CH:13][C:12]([O:15][C@H:16]2[C:24]3[C:19](=[C:20]([OH:26])[CH:21]=[CH:22][C:23]=3[F:25])[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)=[O:5])C.N1C=CC=CC=1.[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[NH4+].[OH-]>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:25][C:23]1[CH:22]=[CH:21][C:20]([O:26][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[C:19]2[C:24]=1[C@H:16]([O:15][C:12]1[CH:13]=[CH:14][C:9]([C@H:7]3[CH2:8][C@@H:6]3[C:4]([OH:3])=[O:5])=[CH:10][CH:11]=1)[CH2:17][CH2:18]2
参加物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 1049PyridineHCID 14923Ammonium HydroxideHCID 66827Phenylboronic AcidHCID 118093712(1S,2S)-2-[4-((R)-7-Fluoro-4-hydroxy-indan-1-yloxy)-phenyl]-cyclopropanecarboxylic acid ethyl ester2 回

生成物 1

HCID 118093716(1S,2S)-2-[4-((R)-7-Fluoro-4-phenoxy-indan-1-yloxy)-phenyl]-cyclopropanecarboxylic acid収率 23.5%

試薬・触媒・溶媒

2
HCID 8895Cupric acetate触媒HCID 6344Dichloromethane溶媒

実験手順

(1S,2S)-2-[4-((R)-7-Fluoro-4-hydroxy-indan-1-yloxy)-phenyl]-cyclopropanecarboxylic acid ethyl ester (Intermediate 5, 150 mg, 0.42 mmol), pyridine (dry; 0.133 mL, 1.68 mmol) and phenylboronic acid (308 mg, 2.53 mmol) are suspended in dichloromethane (10 mL), 4 Å molecular sieves and copper(II)acetate (153 mg, 1.52 mmol) are added and the mixture is stirred under oxygen atmosphere at room temperature for 20 h. NH4OH (2 M aqueous solution, 20 mL) is added and the mixture is extracted with dichloromethane. The organic phase is collected, dried over sodium sulfate and concentrated under vacuum. The crude product is purified by flash chromatography (10-100% ethyl acetate in cyclohexane) to give the title compound (Yield: 40 mg). LC (METHOD 9): tR=2.52 min; Mass spectrum (ES+): m/z=405 [M+H]+.

後処理

  1. extractionthe mixture is extracted with dichloromethane
  2. customThe organic phase is collected
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe crude product is purified by flash chromatography (10-100% ethyl acetate in cyclohexane)

出典と根拠

ORDレコード
ord-7a23061ba52b4d8cabed4ece24c33dde
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09308194B2

反応ノート

読み込み中…

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