Sodium Azide → (3R,5S)-5-(azidomethyl)-3-(3-chloropropyl)pyrrolidin-2-one

HRID 2039952Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2039952
[N+](C1C=CC(S(O[CH2:14][C@@H:15]2[CH2:19][C@@H:18]([CH2:20][CH2:21][CH2:22][Cl:23])[C:17](=[O:24])[NH:16]2)(=O)=O)=CC=1)([O-])=O.[N-:25]=[N+:26]=[N-:27].[Na+].[N-]=[N+]=[N-]>CN(C=O)C>[N:25]([CH2:14][C@H:15]1[NH:16][C:17](=[O:24])[C@H:18]([CH2:20][CH2:21][CH2:22][Cl:23])[CH2:19]1)=[N+:26]=[N-:27]

Komponenten

5

Edukt 3

HCID 33557Sodium AzideHCID 33558AzideHCID 58011487((2S,4R)-4-(3-chloropropyl)-5-oxopyrrolidin-2-yl)methyl 4-nitrobenzenesulfonate

Produkt 1

HCID 86637155(3R,5S)-5-(azidomethyl)-3-(3-chloropropyl)pyrrolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The ((2S,4R)-4-(3-chloropropyl)-5-oxopyrrolidin-2-yl)methyl 4-nitrobenzenesulfonate (18.05 g, 45.2 mmol) and NaN3 (3.23 g, 49.7 mmol, 1.1 equiv) were stirred in 100 mL of DMF for 19 h. After this time a white solid had formed and LC/MS analysis showed formation of the desired azide. The DMF was removed in vacuo and the residue partitioned between EtOAc/H2O (100+100 mL). The mixture was transferred to a separatory funnel and the layers separated. The aqueous layer was extracted with 100 mL additional EtOAc and the combined organic extracts washed with brine, dried over Na2SO4, filtered and evaporated. The (3R,5S)-5-(azidomethyl)-3-(3-chloropropyl)pyrrolidin-2-one was isolated as a pale yellow syrup (9.08 g, 94% yield).

Aufarbeitung

  1. customAfter this time a white solid had formed
  2. customThe DMF was removed in vacuo
  3. customthe residue partitioned between EtOAc/H2O (100+100 mL)
  4. customThe mixture was transferred to a separatory funnel
  5. customthe layers separated
  6. extractionThe aqueous layer was extracted with 100 mL additional EtOAc
  7. washthe combined organic extracts washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-00c371c89e4f46b69828f92f9a0836f4
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580823B2

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