Water → tert-Butyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate

HRID 241564Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 241564
[C:1]([N:8]1[CH2:12][C:11](=O)[CH:10]([C:14]#[N:15])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=O.Cl.[NH2:17][NH2:18].C([O-])(O)=O.[Na+].[OH2:24]>C(O)C>[NH2:15][C:14]1[C:10]2[CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:24])[CH2:12][C:11]=2[NH:17][N:18]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 115031Hydrazinium chlorideHCID 516892Sodium BicarbonateHCID 2756790tert-Butyl 3-cyano-4-oxopyrrolidine-1-carboxylate

Produkt 1

HCID 11333571tert-Butyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

N-Boc-3-cyano-4-pyrrolidinone (5 g, 23.78 mmol) and hydrazine monohydrochloride (1.629 g, 23.78 mmol) were dissolved in ethanol (140 ml). The mixture was heated to 60° C. for 3 h. The mixture was cooled to 0° C. and saturated aqueous NaHCO3 (50 mL) was added slowly, remaining water was extracted four times with ethyl acetate. The organic phase was dried over Na2SO4 (anhydrous). The residue was purified by column chromatography on silica gel Biotage 40M, eluting with EtOAc/MeOH/aqueous ammonia (gradient from 0 to 10%) to give the title product as a yellow foam. LC-MS: 224.99 (M+1).

Aufarbeitung

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionwas extracted four times with ethyl acetate
  3. dry with materialThe organic phase was dried over Na2SO4 (anhydrous)
  4. customThe residue was purified by column chromatography on silica gel Biotage 40M
  5. washeluting with EtOAc/MeOH/aqueous ammonia (gradient from 0 to 10%)

Quellen und Nachweise

ORD-Eintrag
ord-4fff926f718a4d83b4b8008d58bdcee6
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653059B2

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