Trifluoroacetic acid → (R)-Hexahydropyrrolo[1,2-a]pyrazin-3(4H)-one

HRID 421184Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 421184
ClC[C:3]([NH:5][CH2:6][C@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](OC(C)(C)C)=O)=[O:4].C(O)(C(F)(F)F)=O.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[CH2:6]1[NH:5][C:3](=[O:4])[CH2:12][N:8]2[CH2:9][CH2:10][CH2:11][C@H:7]12

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 592157991,1-Dimethylethyl (2R)-2-{[(chloroacetyl)amino]methyl}-1-pyrrolidinecarboxylate

Produkt 1

HCID 55300705(R)-Hexahydropyrrolo[1,2-a]pyrazin-3(4H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

1,1-Dimethylethyl (2R)-2-{[(chloroacetyl)amino]methyl}-1-pyrrolidinecarboxylate (D13; 1.24 g, 4.5 mmol), was dissolved in 20 ml of DCM and treated with TFA (5 ml) at room temperature. After 1 h complete conversion into the desired material was observed and the reaction mixture was loaded onto a SCX cartridge. The product obtained after elution with 2M NH3 in MeOH was then dissolved in acetonitrile (30 ml) and treated with sodium carbonate (1.43 g, 10.34 mmol). The reaction mixture was heated at 60° C. for 6 hours; the crude obtained after removal is purified by flash-chromatography eluting with dichloromethane/MeOH 95/5 affording 250 mg of the desired compound.

Aufarbeitung

  1. customThe product obtained
  2. washafter elution with 2M NH3 in MeOH
  3. dissolutionwas then dissolved in acetonitrile (30 ml)
  4. customthe crude obtained
  5. customafter removal
  6. customis purified by flash-chromatography
  7. washeluting with dichloromethane/MeOH 95/5 affording 250 mg of the desired compound

Quellen und Nachweise

ORD-Eintrag
ord-c7983887726b4f7aad066093383f0151
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097618B2

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