Tetrahydrofuran → HCID 9815102, Verbindung

HRID 983905Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 983905
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:15]3[C:11]([CH2:12][CH2:13][CH2:14]3)=[C:10]([C:16](OCC)=[O:17])[C:9]=2[C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)=[CH:4][CH:3]=1.C1COCC1>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:15]3[C:11]([CH2:12][CH2:13][CH2:14]3)=[C:10]([CH2:16][OH:17])[C:9]=2[C:21]2[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 8028TetrahydrofuranHCID 9946393Ethyl 3-(4-fluorophenyl)-2-(4-pyridyl)-6,7-dihydro-5H-pyrrolizine-1-carboxylate

Produkt 1

HCID 9815102HCID 9815102, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Ethyl 3-(4-fluorophenyl)-2-(4-pyridyl)-6,7-dihydro-5H-pyrrolizine-1-carboxylate (example 1A, 4.56 g, 13 mmol) is dissolved in abs. THF (100 ml) under argon and Na bismethoxyethoxyaluminum hydride (VitrideR) is added dropwise through a septum via the cannula of a syringe (20 min). The mixture is stirred at 50° C. for 2 h, whereupon starting material is no longer detectable by tlc (Al2O3—ethyl acetate/n-hexane 3:7), then it is allowed to cool. H2O (25 ml) is cautiously added dropwise to the reaction solution, then it is concentrated in vacuo (THF evaporates), and the aqueous organic residue is treated with ethyl acetate (100 ml). The phases are separated. The organic phase is washed 2 times with water (40 ml), dried over Na2SO4 sicc. and concentrated in vacuo (5.0 g). The reddish brown-colored, resinous residue is crystallized from diethyl ether (10 ml). The crystals are washed with ethyl acetate (5 ml) and ether (5 ml) and dried. 3.67 g of the compound sought remain

Aufarbeitung

  1. temperatureto cool
  2. concentrationit is concentrated in vacuo (THF evaporates)
  3. additionthe aqueous organic residue is treated with ethyl acetate (100 ml)
  4. customThe phases are separated
  5. washThe organic phase is washed 2 times with water (40 ml)
  6. dry with materialdried over Na2SO4 sicc
  7. concentrationand concentrated in vacuo (5.0 g)
  8. customThe reddish brown-colored, resinous residue is crystallized from diethyl ether (10 ml)
  9. washThe crystals are washed with ethyl acetate (5 ml) and ether (5 ml)
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-463266a2f6f7453f950fe76e1a1be0ba
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06867211B2

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