Benzyl chloroformate → 1-Benzyloxycarbonyl-4-(S)-(1-ethoxycarbonylcyclopropyl)-3-(S)-fluoropyrrolidine

HRID 635105Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 635105
[CH2:1]([O:3][C:4]([C:6]1([C@H:9]2[CH2:13][N:12]([C@H](C3C=CC=CC=3)C)[CH2:11][C@H:10]2[F:22])[CH2:8][CH2:7]1)=[O:5])[CH3:2].Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>ClCCl>[CH2:27]([O:26][C:24]([N:12]1[CH2:13][C@H:9]([C:6]2([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:8][CH2:7]2)[C@H:10]([F:22])[CH2:11]1)=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Komponenten

4

Edukt 2

HCID 10387Benzyl chloroformateHCID 109687574-(S)-(1Ethoxycarbonylcyclopropyl)-3-(S)-fluoro-1-[1-(S)-phenylethyl]pyrrolidine

Produkt 1

HCID 110350361-Benzyloxycarbonyl-4-(S)-(1-ethoxycarbonylcyclopropyl)-3-(S)-fluoropyrrolidineAusbeute 83,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-(S)-(1-Ethoxycarbonylcyclopropyl)-3-(S)-fluoro-1-(1-(S)-phenylethyl]pyrrolidine (5.08 g, 16.63 mmol) was dissolved in dry dichloromethane (50 ml). Under ice cooling, benzyl chloroformate (3.56 ml, 25.0 mmol) was added dropwise into this solution. Then the liquid reaction mixture was heated under reflux for 1 hour and dichioromethane was evaporated under reduced pressure. The residue was subjected. to flash silica gel column chromatography (eluent: n-hexane:ethyl acetate=3:1) to obtain 4.67 g (83.7%) of the title compound as a colorless oily substance.

Aufarbeitung

  1. customThen the liquid reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 1 hour
  4. customdichioromethane was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-42cff8cd194040a9b8ad4c7e0533a4bc
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06184388B2

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