Dimethyl Sulfoxide → 1-N-Cbz-3-pyrrolidinone

HRID 129508

Reaktionsgleichung

Reaktionsgleichung von HRID 129508
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:18][C:19]([N:21]1[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22]1)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>O>[CH2:11]([O:18][C:19]([N:21]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22]1)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 560953Benzyl 3-hydroxypyrrolidine-1-carboxylate

Produkt 1

HCID 5612031-N-Cbz-3-pyrrolidinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

150 ml of oxalic acid chloride was added to 2 liters of dichloromethylene. 245 ml of dimethylsulfoxide was gradually added at -70° to -50° C. in a stream of argon. 70.67 g of N-(N-(benzyloxycarbonyl)-3-pyrrolidinol dissolved in dichloromethylene was dropped. After gradual dropping of 720 ml of triethylamine, the mixture was raised to room temperature. After completion of the reaction, the reaction solution was poured into water and extracted with dichloromethylene, followed by removal of the solvent by distillation under reduced pressure. The residue was purified by column chromatography (eluting solvent: hexane-ethyl acetate), thereby obtaining 66.55 g of the intended compound.

Aufarbeitung

  1. additionwas dropped
  2. customAfter completion of the reaction
  3. extractionextracted with dichloromethylene
  4. customfollowed by removal of the solvent by distillation under reduced pressure
  5. customThe residue was purified by column chromatography (eluting solvent: hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-ea7c1b7701d14646b5be5ae07b542132
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05468740

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