Hydrogen Peroxide → (1S,2S)-2-[4-((R)-7-Fluoro-4-hydroxy-indan-1-yloxy)-phenyl]-cyclopropanecarboxylic acid ethyl ester

HRID 625686ノート

反応式

HRID 625686 の反応式
[CH2:1]([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](B4OC(C)(C)C(C)(C)O4)[CH:21]=[CH:22][C:23]=3[F:25])[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)=[O:5])[CH3:2].[OH:35]O>C(O)(=O)C.O>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:8][C@@H:7]1[C:9]1[CH:10]=[CH:11][C:12]([O:15][C@H:16]2[C:24]3[C:19](=[C:20]([OH:35])[CH:21]=[CH:22][C:23]=3[F:25])[CH2:18][CH2:17]2)=[CH:13][CH:14]=1)=[O:5])[CH3:2]

参加物

5

反応物 2

HCID 784Hydrogen PeroxideHCID 86703891(1S,2S)-2-{4-[(R)-7-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-indan-1-yloxy]-phenyl}-cyclopropanecarboxylic acid ethyl ester2 回

生成物 1

HCID 118093712(1S,2S)-2-[4-((R)-7-Fluoro-4-hydroxy-indan-1-yloxy)-phenyl]-cyclopropanecarboxylic acid ethyl ester収率 95.2%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

(1S,2S)-2-{4-[(R)-7-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-indan-1-yloxy]-phenyl}-cyclopropanecarboxylic acid ethyl ester (Intermediate 4, 1.31 g, 2.8 mmol) is suspended in acetic acid (8 mL) and hydrogen peroxide solution (35% in water, 0.97 mL, 11.2 mmol) is added. The mixture is stirred for 1 hour then diluted with water and extracted with ethyl acetate. The organic extracts are washed with water and brine, dried over sodium sulfate and the solvent removed. The residue is dried under vacuum to give the title compound (Yield 0.95 g). LC (METHOD 6): tR=0.57 min; Mass spectrum (ES+): m/z=357 [M+H]+.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts are washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent removed
  5. customThe residue is dried under vacuum

出典と根拠

ORDレコード
ord-840bbde3999c42cbbae075242af48cc7
出典データセット
uspto-grants-2016_04
特許番号
US09308194B2

反応ノート

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