Water → (2R,4R)-1-[(tert-butoxy)carbonyl]-4-methoxypyrrolidine-2-carboxylic acid

HRID 1796302Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1796302
C[O:2][C:3]([C@H:5]1[CH2:9][C@@H:8]([O:10][CH3:11])[CH2:7][N:6]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:4].O.O[Li].O>C(#N)C>[C:15]([O:14][C:12]([N:6]1[CH2:7][C@H:8]([O:10][CH3:11])[CH2:9][C@@H:5]1[C:3]([OH:4])=[O:2])=[O:13])([CH3:18])([CH3:16])[CH3:17]

Komponenten

5

Edukt 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 541382851-(Tert-butyl) 2-methyl (2R,4R)-4-methoxypyrrolidine-1,2-dicarboxylate

Produkt 1

HCID 11459222(2R,4R)-1-[(tert-butoxy)carbonyl]-4-methoxypyrrolidine-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Into a solution of 5 (2.54 g, 9.80 mmol) in acetonitrile (20 mL) was added water (20 mL) and LiOH.H2O (1.64 g, 39.2 mmol). The mixture was stirred at RT for 28 h before removing the acetonitrile under reduced pressure. EtOAc was added to the residue that was then washed with 1N HCl. The aqueous layer was extracted with additional EtOAc and the combined organic layers were washed with brine and dried over MgSO4. The solution was concentrated under reduced pressure to reveal 6 (2.16 g, 90%) as a white solid. MS: APCI (AP−): 244.1 (M)−.

Aufarbeitung

  1. custombefore removing the acetonitrile under reduced pressure
  2. additionEtOAc was added to the residue that
  3. washwas then washed with 1N HCl
  4. extractionThe aqueous layer was extracted with additional EtOAc
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationThe solution was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8642c9fe3b764e219e1372da0a01db28
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07030141B2

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