p-Fluoronitrobenzene → 1,1-Dimethylethyl (3R)-3-(4-nitrophenoxy)-1-pyrrolidinecarboxylate

HRID 715772ノート

反応式

HRID 715772 の反応式
[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1.[OH-].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[N+:21]([C:18]1[CH:19]=[CH:20][C:15]([O:1][C@@H:2]2[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]2)=[CH:16][CH:17]=1)([O-:23])=[O:22]

参加物

6

反応物 3

HCID 9590p-FluoronitrobenzeneHCID 14797Potassium HydroxideHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylate

生成物 1

HCID 532557081,1-Dimethylethyl (3R)-3-(4-nitrophenoxy)-1-pyrrolidinecarboxylate

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 962Water溶媒

反応条件

温度
40 °C

実験手順

(R)-Tert-butyl 3-hydroxypyrrolidine-1-carboxylate (10 g, 53.4 mmol) was dissolved in 1-fluoro-4-nitrobenzene (13.94 g, 99 mmol). An aqueous solution of 5.9N potassium hydroxide (77 ml, 452 mmol) was added followed by addition of tetrabutylammonium bromide (2.238 g, 6.94 mmol). The reaction mixture was stirred at 40° C. for 24 hours, cooled, diluted with water and extracted with ethyl acetate. The combined organic layers were dried with sodium sulfate, filtered and concentrated to give the title compound.

後処理

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-7fc6041628394057be052f88c02b69c6
出典データセット
uspto-grants-2015_11
特許番号
US09187472B2

反応ノート

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