Trifluoroacetic acid → (5R)-5-[(5-Chloro-6-methoxypyridin-2-yl)ethynyl]pyrrolidin-2-one

HRID 70536ノート

反応式

HRID 70536 の反応式
FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1.[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([C:25]#[C:26][C@@H:27]2[N:31](CC3C=CC(OC)=CC=3OC)[C:30](=[O:43])[CH2:29][CH2:28]2)=[N:21][C:22]=1[O:23][CH3:24]>>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([C:25]#[C:26][C@@H:27]2[NH:31][C:30](=[O:43])[CH2:29][CH2:28]2)=[N:21][C:22]=1[O:23][CH3:24]

参加物

4

反応物 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 58452822(5R)-5-[(5-Chloro-6-methoxypyridin-2-yl)ethynyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one

生成物 1

HCID 58452568(5R)-5-[(5-Chloro-6-methoxypyridin-2-yl)ethynyl]pyrrolidin-2-one収率 82%

反応条件

温度
80 °C

実験手順

Trifluoroacetic acid (4 mL) and anisole (2 mL) were added to (5R)-5-[(5-chloro-6-methoxypyridin-2-yl)ethynyl]-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one (457 mg), and the mixture was stirred at 80° C. for two hours. The reaction solution was concentrated, and the residue was diluted with chloroform, washed with saturated aqueous sodium bicarbonate and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1) to give the title compound as a colorless oil (234 mg, 82%).

後処理

  1. concentrationThe reaction solution was concentrated
  2. additionthe residue was diluted with chloroform
  3. washwashed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1)

出典と根拠

ORDレコード
ord-f892af96d00c421e9e067aca38e9ec4c
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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