Ethanol → 6-Fluoro-5-(hydroxymethyl)indolin-2-one

HRID 1094020ノート

反応式

HRID 1094020 の反応式
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][C:3]=1[C:12](OC)=[O:13].CCO.[Li+].[BH4-]>C1COCC1>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][C:3]=1[CH2:12][OH:13]

参加物

5

反応物 3

HCID 702Ethanol2 回HCID 4148881Lithium borohydride3 回HCID 66636241methyl 6-fluoro-2-oxo-2,3-dihydro-1H-indole-5-carboxylate

生成物 1

HCID 666363046-Fluoro-5-(hydroxymethyl)indolin-2-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of the compound obtained in Step B (2.68 mmoles) in anhydrous THF (20 mL) is maintained under nitrogen in the presence of 0.3 mL of EtOH. The solution is cooled to 0° C. and then 5.28 mmol of LiBH4 are added. The reaction mixture is stirred for 2 hours at ambient temperature; a second portion of LiBH4 (6.20 mmol) is then added and stirring is maintained for a further 3 hours. EtOH (0.3 mL) and a third portion of LiBH4 (9.14 mmol) are added and the reaction mixture is stirred overnight. The reaction mixture is quenched with 10 mL of water, and then saturated aqueous NH4Cl solution (30 mL) is added. Extraction with EtOAc is carried out, and the organic phases are dried over Na2SO4, filtered and evaporated in vacuo. The residue obtained is purified by flash chromatography (DCM/MeOH 10:1) to yield the title product.

後処理

  1. stirringstirring
  2. temperatureis maintained for a further 3 hours
  3. stirringthe reaction mixture is stirred overnight
  4. customThe reaction mixture is quenched with 10 mL of water
  5. additionsaturated aqueous NH4Cl solution (30 mL) is added
  6. extractionExtraction with EtOAc
  7. dry with materialthe organic phases are dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe residue obtained
  11. customis purified by flash chromatography (DCM/MeOH 10:1)

出典と根拠

ORDレコード
ord-e0985f98c6d441f98c8c077a43f1d933
出典データセット
uspto-grants-2012_03
特許番号
US08133889B2

反応ノート

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