N-bromobutanimide → N-Ethylcarbamate 5-methyl-6-bromo-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

HRID 1517699Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1517699
C1C(=O)N([Br:8])C(=O)C1.[CH2:9]([NH:11][C:12](=[O:14])[O-:13])[CH3:10].[CH3:15][C:16]1[CH:17]=[CH:18][C:19]2[CH:20]([CH3:28])[CH:21]3[CH2:25][NH:24][CH2:23][CH:22]3[C:26]=2[CH:27]=1>C(#N)C.C(Cl)Cl.O>[CH2:9]([NH:11][C:12](=[O:13])[O-:14])[CH3:10].[CH3:15][C:16]1[C:17]([Br:8])=[CH:18][C:19]2[CH:20]([CH3:28])[CH:21]3[CH2:25][NH:24][CH2:23][CH:22]3[C:26]=2[CH:27]=1

Komponenten

6

Edukt 2

HCID 67184N-bromobutanimideHCID 86602856HCID 86602856, Verbindung

Produkt 1

HCID 86602858N-Ethylcarbamate 5-methyl-6-bromo-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

NBS (34 mg, 0.2 mmol) was added to a solution of N-Ethylcarbamate-5-methyl-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (from Example 21, Step A) (50 mg, 0.2 mmol) in acetonitrile (1 mL), and stirred overnight at room temperature. The reaction was diluted with CH2Cl2 (3 mL) and H2O (3 mL) and filtered through an Extrelut column. The column was washed with CH2Cl2 and the filtrate was concentrated. The crude product was purified by column chromatography (SiO2) using a 0-50% EtOAc—hexanes gradient to afford the subtitle compound. MS calculated for C16H20BrNO2+H: 338, observed: 338.

Aufarbeitung

  1. filtrationfiltered through an Extrelut column
  2. washThe column was washed with CH2Cl2
  3. concentrationthe filtrate was concentrated
  4. customThe crude product was purified by column chromatography (SiO2)

Quellen und Nachweise

ORD-Eintrag
ord-7d402f8be4414f358cbd5917909725e6
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232311B2

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