Ethanol → Ethyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochloride

HRID 365328

Reaktionsgleichung

Reaktionsgleichung von HRID 365328
S(Cl)([Cl:3])=O.[OH:5][C@H:6]1[CH2:10][NH:9][C@@H:8]([C:11]([OH:13])=[O:12])[CH2:7]1.[CH2:14](O)[CH3:15]>>[ClH:3].[CH2:14]([O:12][C:11]([C@H:8]1[CH2:7][C@@H:6]([OH:5])[CH2:10][NH:9]1)=[O:13])[CH3:15]

Komponenten

4

Edukt 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 440014Cis-4-Hydroxy-D-Proline

Produkt 1

HCID 12709308Ethyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochloride

Versuchsvorschrift

3.27 g (27.5 mmol) of thionyl chloride was added dropwise to a suspension of cis-4-hydroxy-D-proline (3.00 g, 2.9 mmol) in ethanol (15 ml) and the mixture was refluxed for 2 hours. The mixture was concentrated, acetone was added to the residue and the solution was cooled on ice. The resultant precipitate was filtered and 4.23 g of (2R,4R)-(+)-2-(ethoxycarbonyl)-4-hydroxypyrrolidine hydrochloride was obtained as colorless needles (94.5%).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 2 hours
  2. concentrationThe mixture was concentrated
  3. additionacetone was added to the residue
  4. temperaturethe solution was cooled on ice
  5. filtrationThe resultant precipitate was filtered

Quellen und Nachweise

ORD-Eintrag
ord-c9fda451c4c64a4baef159b8914061f8
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06127361

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