1,8-Diazabicyclo(5.4.0)undec-7-ene → 1055306-64-3

HRID 1426689Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1426689
Br[CH2:2][CH:3]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:5](=[O:15])[C:4]1([F:17])[F:16].N12CCCN=C1CCCCC2>O1CCCC1>[F:17][C:4]1([F:16])[C:3](=[CH2:2])[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])[C:5]1=[O:15]

Komponenten

4

Edukt 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 59826883Tert-butyl 4-(bromomethyl)-3,3-difluoro-2-oxopyrrolidine-1-carboxylate

Produkt 1

HCID 598268761055306-64-3Ausbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 4-(bromomethyl)-3,3-difluoro-2-oxopyrrolidine-1-carboxylate (50.1 g) in tetrahydrofuran (400 mL) was added dropwise 1,8-diazabicyclo[5.4.0]undec-7-ene (25.0 mL) at 0° C. over 15 min. After the completion of the dropwise addition, the mixture was stirred at room temperature for 1 hr. Insoluble materials were filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane:ethyl acetate=4:1). The obtained crystals were washed with diisopropyl ether to give the title compound as colorless crystals (yield 28.1 g, 76%).

Aufarbeitung

  1. additionAfter the completion of the dropwise addition
  2. filtrationInsoluble materials were filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: hexane:ethyl acetate=4:1)
  5. washThe obtained crystals were washed with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-67447c9b1604489a8606fe3d57a37ccc
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933105B2

Notizen zur Reaktion

Wird geladen…