Ethyl Acetate → tert-butyl (RS)-3-(4-amino-3-chlorophenyl)pyrrolidine-1-carboxylate

HRID 571832Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 571832
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]2)=[CH:4][CH:3]=1.C1C(=O)N([Cl:27])C(=O)C1.CCOC(C)=O>CN(C=O)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9]2)=[CH:6][C:7]=1[Cl:27]

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 31398ChlorosuccinimideHCID 573650691,1-Dimethylethyl 3-(4-aminophenyl)-1-pyrrolidinecarboxylate

Produkt 1

HCID 86674689tert-butyl (RS)-3-(4-amino-3-chlorophenyl)pyrrolidine-1-carboxylateAusbeute 51,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a stirred solution of tert-butyl 3-(4-aminophenyl)pyrrolidine-1-carboxylate (2.00 g, CAS-908334-28-1) in DMF (15 ml) was added NCS (1.07 g) and the mixture was stirred at 70° C. for 1 hour. The reaction mixture was then cooled to room temperature and poured into EtOAc and extracted sequentially with water and with saturated brine. The organic layer was dried over Na2SO4 and then concentrated in vacuo. The residue was purified by column chromatography (SiO2, gradient: 0% to 55% EtOAc in hexanes) to afford tert-butyl (RS)-3-(4-amino-3-chlorophenyl)pyrrolidine-1-carboxylate (1.16 g, 51%) as a yellow oil which was used in the next step without further purification. MS (ISP): 299.0 ([{37Cl}M+H]+), 297.2 ([{35Cl}M+H]+), 243.0 ([{37Cl}M+H—C4H8]+), 241.1 ([{35Cl}M+H—C4H8]+).

Aufarbeitung

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. extractionextracted sequentially with water and with saturated brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (SiO2, gradient: 0% to 55% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-280683f9e61f4b5cabad774882068a1d
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029370B2

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