Water → 1,3-Pyrrolidinedicarboxylic acid, 5-methyl-, 1-(1,1-dimethylethyl) ester

HRID 2367314Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2367314
[CH3:1][CH:2]1[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:5][CH:4]([C:14]([O:16]CC)=[O:15])[CH2:3]1.O[Li].O.O>C1COCC1>[CH3:11][C:10]([O:9][C:7]([N:6]1[CH:2]([CH3:1])[CH2:3][CH:4]([C:14]([OH:16])=[O:15])[CH2:5]1)=[O:8])([CH3:12])[CH3:13]

Komponenten

5

Edukt 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 19894765HCID 19894765, Verbindung

Produkt 1

HCID 585047701,3-Pyrrolidinedicarboxylic acid, 5-methyl-, 1-(1,1-dimethylethyl) ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1-(1,1-Dimethylethyl) 3-ethyl 5-methyl-1,3-pyrrolidinedicarboxylate (1.0 g, 3.89 mmol, an estimated 3:1 mixture of cis/trans isomers) and LiOH.H2O (228 mg, 5.44 mmol, 1.4 equiv) was stirred in THF (5 mL) and water (2 mL) as a two-phase mixture at room temperature for 18 hours. The mixture was concentrated in vacuo, and the resulting residue was taken up in 15 mL of water, acidified with cold 2N HCl, and extracted with 2×50 mL of EtOAc. The organic were dried over Na2SO4, filtered and concentrated in vacuo to afford the title compound (1.03 g) as an oil. LC-MS (ES) m/z=230 [M+H]+.

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. extractionextracted with 2×50 mL of EtOAc
  3. dry with materialThe organic were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a98aba7aa71147a7a1821afe8e008a08
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697685B2

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