Methanol → (2R,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate

HRID 1740472

Reaktionsgleichung

Reaktionsgleichung von HRID 1740472
CO.[C:3](Cl)(=O)C.[OH:7][C@H:8]1[CH2:12][NH:11][C@@H:10]([C:13]([OH:15])=[O:14])[CH2:9]1>CCOCC>[C:13]([C@H:10]1[CH2:9][C@@H:8]([OH:7])[CH2:12][NH:11]1)([O:15][CH3:3])=[O:14]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 6367Acetyl chlorideHCID 440014Cis-4-Hydroxy-D-Proline

Produkt 1

HCID 7020012(2R,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

In a 250 ml round bottom flask equipped with a magnetic stir bar and a reflex condenser were placed dry methanol (40 ml) and cooled in ice bath under argon atmosphere. To this stirred solution was added acetyl chloride (4.32 g, 55 mmol) followed by cis-4-hydroxy-D-proline 34 (5.00 g, 38.17 mmol). The resulting solution was heated at reflex for 7-8 h and cooled to room temperature. The solution was diluted with ether, and the resulting white solid was collected by suction, was with ether and dried under vacuum over solid NaOH. Yield; 6.9 g (100%) . 1HNMR (CDCl3): 2.09 (2 dd, 1H), 2.34 (m, 1H), 3.49-3.73 (m, 3H), 3.79 (s, 3H, CH3), 4.34 (m, 2H)

Aufarbeitung

  1. customIn a 250 ml round bottom flask equipped with a magnetic stir bar and a reflex condenser
  2. temperaturecooled in ice bath under argon atmosphere
  3. temperatureThe resulting solution was heated at reflex for 7-8 h
  4. customthe resulting white solid was collected by suction
  5. dry with materialdried under vacuum over solid NaOH

Quellen und Nachweise

ORD-Eintrag
ord-14077d5573a9437ea45810455337a0bb
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05969135

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