Methanol → Methyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochloride

HRID 732349

Reaktionsgleichung

Reaktionsgleichung von HRID 732349
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.[CH3:14]O>>[ClH:3].[CH3:14][O:12][C:11]([C@H:8]1[CH2:7][C@@H:6]([OH:5])[CH2:10][NH:9]1)=[O:13]

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 440014Cis-4-Hydroxy-D-Proline

Produkt 1

HCID 12764090Methyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochlorideAusbeute 82 %

Versuchsvorschrift

Add thionyl chloride (5.5 mL, 75.8 mmol) to an ice-cold suspension of 4-(R)-hydroxypyrrolidine-2-(R)-carboxylic acid (4.97 g, 31.9 mmol) in methanol (60 mL). Stir 10 min, then warm to room temperature and stir 3.5 h. Concentrate, add methanol, and concentrate again. Dissolve in absolute ethanol (25 mL) and precipitate with diethyl ether (50 mL) and filter. Dry cake under vacuum to give the title compound as a white solid (4.77 g, 82%).

Aufarbeitung

  1. stirringstir 3.5 h
  2. concentrationConcentrate
  3. additionadd methanol
  4. concentrationconcentrate again
  5. dissolutionDissolve in absolute ethanol (25 mL)
  6. customprecipitate with diethyl ether (50 mL)
  7. filtrationfilter
  8. customDry cake under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ca476a49923b4c1c88f3da697bd0a4b9
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585885B2

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