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

HRID 717932Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 717932
[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]

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

(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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-105dc9809c234fa29438d6d4882f5188
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09193723B2

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