Potassium Carbonate → (S)-tert-butyl 4-(3-(4-bromo-2-fluorophenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate

HRID 407879ノート

反応式

HRID 407879 の反応式
CS([O:5][C@@H:6]1[CH2:10][CH2:9][N:8]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[C:7]1=[O:24])(=O)=O.[Br:25][C:26]1[CH:31]=[CH:30][C:29](O)=[C:28]([F:33])[CH:27]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[Br:25][C:26]1[CH:31]=[CH:30][C:29]([O:5][C@H:6]2[CH2:10][CH2:9][N:8]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[C:7]2=[O:24])=[C:28]([F:33])[CH:27]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 27249814-Bromo-2-fluorophenolHCID 86688072(R)-tert-butyl 4-(3-(methylsulfonyloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate

生成物 1

HCID 86688077(S)-tert-butyl 4-(3-(4-bromo-2-fluorophenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate収率 84%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
70 °C

実験手順

(R)-tert-Butyl 4-(3-(methylsulfonyloxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (Preparation D; 1.7 g, 4.7 mmol) was dissolved in dry DMSO (30 mL) and 4-bromo-2-fluorophenol (1.1 g, 5.6 mmol) and K2CO3 (0.78 g, 5.6 mmol) was added and the reaction heated to 70° C. under nitrogen. The reaction became purple then black. The reaction was cooled to ambient temperature after 3 hours and partitioned between water and EtOAc, extracted with EtOAc, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified over silica gel (40% EtOAc in hexanes) to afford (S)-tert-butyl 4-(3-(4-bromo-2-fluorophenoxy)-2-oxopyrrolidin-1-yl)piperidine-1-carboxylate (1.8 g, 3.9 mmol, 84% yield) as a white solid.

後処理

  1. temperatureThe reaction was cooled to ambient temperature after 3 hours
  2. custompartitioned between water and EtOAc
  3. extractionextracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified over silica gel (40% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-7f141bf48955487790f07a31bf7c3e3f
出典データセット
uspto-grants-2014_06
特許番号
US08754226B2

反応ノート

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