Pyrrolidine → HCID 62177350, Verbindung

HRID 1916620Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1916620
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:6][NH:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C1COCC1.C(O)(=O)C>[CH3:6][NH:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17]

Komponenten

7

Edukt 4

HCID 31268PyrrolidineHCID 516892Sodium BicarbonateHCID 38542614-(methylamino)-3-nitrobenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 62177350HCID 62177350, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5.55 g (78.0 mmol) pyrrolidine are added to a solution of 4.70 g (26.1 mmol) 4-methylamino-3-nitro-benzaldehyde in 100 mL THF and the reaction mixture is acidified with glacial acetic acid. 6.36 g (30.0 mmol) NaBH(OAc)3 are added and the reaction mixture is stirred overnight at RT. The mixture is combined with saturated NaHCO3 solution and the aqueous phase is extracted twice with EtOAc. The combined organic extracts are washed with 200 mL semisaturated NaHCO3 solution and dried over MgSO4. The solvent is eliminated i.vac. and further purification is carried out by column chromatography on silica gel (gradient: DCM to DCM/MeOH 9:1).

Aufarbeitung

  1. extractionthe aqueous phase is extracted twice with EtOAc
  2. washThe combined organic extracts are washed with 200 mL
  3. dry with materialdried over MgSO4
  4. customand further purification

Quellen und Nachweise

ORD-Eintrag
ord-33ef7ad9873d47acb3ee82c9b720e312
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618132B2

Notizen zur Reaktion

Wird geladen…