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Sodium borohydride → 2-(3-Fluorophenyl)pyrrolidine

HRID 1594689
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1594689
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH2:9][CH2:10][CH2:11][N:12]=2)[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:9][CH2:10][CH2:11][NH:12]2)[CH:5]=[CH:6][CH:7]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydride2×HCID 120090495-(3-fluorophenyl)-3,4-dihydro-2H-pyrrole

Produkt 1

HCID 39124022-(3-Fluorophenyl)pyrrolidineAusbeute 69,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 5-(3-fluoro-phenyl)-3,4-dihydro-2H-pyrrole (1.10 g, 6.74 mmol) in methanol (40 ml) was added at 0° C. sodium borohydride (0.51 g, 13.4 mmol) and the reaction mixture was stirred at RT for 1 h. Then additional sodium borohydride (0.25 g, 6.61 mmol) was added and stirring was continued for 1 h. The mixture was evaporated, dissolved in saturated NaHCO3-solution (70 ml) and extracted with dichloromethane (2×70 ml). The combined organic layers were washed with brine (70 ml), dried (MgSO4) and evaporated. The crude product was purified by column chromatography on silica gel (dichloromethane/MeOH/NH4OH 15:1:0.1) to give the product (0.77 g, 69%) as a colorless oil, MS: m/e=165 (M+).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued for 1 h
  3. customThe mixture was evaporated
  4. dissolutiondissolved in saturated NaHCO3-solution (70 ml)
  5. extractionextracted with dichloromethane (2×70 ml)
  6. washThe combined organic layers were washed with brine (70 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe crude product was purified by column chromatography on silica gel (dichloromethane/MeOH/NH4OH 15:1:0.1)

Quellen und Nachweise

ORD-Eintrag
ord-433d9dd8e2504b82994092988a61f437
Quelldatensatz
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06284785B1

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