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

HRID 715772노트

반응식

HRID 715772 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매

반응 조건

온도
40 °C

실험 절차

(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.

후처리

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

출처 및 근거

ORD 기록
ord-7fc6041628394057be052f88c02b69c6
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187472B2

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