Lithium Hydroxide → 1-[(Benzyloxy)carbonyl]-3-methylpyrrolidine-3-carboxylic acid

HRID 408257Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 408257
[CH3:1][C:2]1([C:17]([O:19]C)=[O:18])[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.[Li+].[OH-]>C(O)C>[CH2:10]([O:9][C:7]([N:4]1[CH2:5][CH2:6][C:2]([CH3:1])([C:17]([OH:19])=[O:18])[CH2:3]1)=[O:8])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 602052351-Benzyl 3-methyl 3-methylpyrrolidine-1,3-dicarboxylate

Produkt 1

HCID 602052341-[(Benzyloxy)carbonyl]-3-methylpyrrolidine-3-carboxylic acidAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
78 °C

Versuchsvorschrift

1-Benzyl 3-methyl 3-methylpyrrolidine-1,3-dicarboxylate (2.72 g, 9.81 mmol) in ethanol (15 mL) was added to a 3M LiOH solution (14.7 mL, 29.4 mmol), and the reaction mixture was stirred at 78° C. (bath) for 1 hour. The ethanol was removed and, ether (30 mL) was added. The aqueous layer was separated and acidified with saturated potassium hydrogen sulfate to a pH of about 3 to about 4, extracted with ethyl acetate (50 mL), washed with brine and dried over sodium sulfate. After removal of the solvent, 1-(benzyloxycarbonyl)-3-methylpyrrolidine-3-carboxylic acid (2.56 g, 99% yield) was isolated as an oil.

Aufarbeitung

  1. customThe ethanol was removed
  2. additionether (30 mL) was added
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate (50 mL)
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. customAfter removal of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-fcf2eeca7fa24a9cad0b644812d2a50a
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08758830B2

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