4-Chloro-2-nitrobenzaldehyde → HCID 66758130, Verbindung

HRID 242624

Reaktionsgleichung

Reaktionsgleichung von HRID 242624
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[C:17]([N+:23]([O-:25])=[O:24])[CH:16]=1.[BH4-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([NH:13][CH2:19][C:18]2[CH:21]=[CH:22][C:15]([Cl:14])=[CH:16][C:17]=2[N+:23]([O-:25])=[O:24])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 796744-Chloro-2-nitrobenzaldehydeHCID 27563701-Boc-3-aminopyrrolidineHCID 4311764Sodium borohydride

Produkt 1

HCID 66758130HCID 66758130, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 3-Amino-pyrrolidine-1-carboxylic acid tert-butyl ester (2 g, 10.7 mmol) in methanol (20 mL) was added 4-Chloro-2-nitro-benzaldehyde (1.98 g, 10.7 mmol). The resultant solution was heated at 60° C. overnight. The reaction mixture was cooled to 0° C. and to it was added NaBH4 (629 mg, 10 mmol). After 1 h, the reaction solution was quenched with saturated NaHCO3 solution and extracted with ethyl acetate. The organic extract was dried over MgSO4, filtered and concentrated to provide the crude product as an oil. The crude product was used in the subsequent reaction without further purification. LCMS (retention time=1.28, ES+; 356)

Aufarbeitung

  1. customthe reaction solution was quenched with saturated NaHCO3 solution
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-816b0c49c9614adb8740b35af458b82f
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653096B2

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