Acetic Acid → 5-Methyl-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

HRID 1020323Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1020323
C1C(=O)N([Cl:8])C(=O)C1.C(O)(=O)C.C(NC(=O)[O-])C.[CH3:19][C:20]1[CH:21]=[CH:22][C:23]2[CH:24]([CH3:32])[CH:25]3[CH2:29][NH:28][CH2:27][CH:26]3[C:30]=2[CH:31]=1>ClCCCl.C(Cl)Cl.O>[CH3:19][C:20]1[C:21]([Cl:8])=[CH:22][C:23]2[CH:24]([CH3:32])[CH:25]3[CH2:29][NH:28][CH2:27][CH:26]3[C:30]=2[CH:31]=1

Komponenten

7

Edukt 3

HCID 176Acetic AcidHCID 31398ChlorosuccinimideHCID 86602856HCID 86602856, Verbindung

Produkt 1

HCID 585988585-Methyl-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

NCS (27 mg, 0.2 mmol) and acetic acid (1 mL) were added to a solution of N-Ethylcarbamate-5-methyl-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (50 mg, 0.2 mmol) in DCE (1 mL). The reaction solution was stirred for 3 hours at 60° C. 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 0-60% ethyl acetate-hexanes gradient to afford the subtitle compound. MS calculated for C16H20ClNO2+H: 294, observed: 294.

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-fc5ed8e2d36c484ba721115f05787ddd
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716324B2

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