Lithium Hydroxide → (2S,4S)-4-azido-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid

HRID 884045Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 884045
[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]=[N+:14]=[N-:15])[CH2:10][C@H:9]1[C:16]([O:18]C)=[O:17])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Li+].[OH-]>CO.O>[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]=[N+:14]=[N-:15])[CH2:10][C@H:9]1[C:16]([OH:18])=[O:17])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 11219435(2S,4S)-1-tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylate

Produkt 1

HCID 12094910(2S,4S)-4-azido-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidAusbeute 100,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Methyl (2S,4S)-1-Boc-4-azidopyrrolidine-2-carboxylate (10 g, 37 mmol) obtained in Step D of Preparation 1 was dissolved in MeOH (100 mL) and water (100 mL). LiOH (2.5 g, 111 mmol) was added thereto. The reaction solution was stirred for 3 hours at room temperature, concentrated in vacuo and acidify with 1N HCl. The solution was extracted with EtOAc. The extracted organic solution was washed with brine, dried over MgSO4 and concentrated in vacuo to give the title compound (9.5 g, 95%).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. extractionThe solution was extracted with EtOAc
  3. washThe extracted organic solution was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c3a5d4c8c6af414f8097a8220f6252b5
Quelldatensatz
uspto-grants-2012_08
Patentnummer
US08236955B2

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