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Potassium Carbonate → N-Ethylcarbamate 5-(4-fluorobenzyloxy)-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

HRID 1517686
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1517686
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:16]([NH:18][C:19](=[O:21])[O-:20])[CH3:17].[OH:22][C:23]1[C:24]([Cl:36])=[CH:25][C:26]2[CH:27]([CH3:35])[CH:28]3[CH2:32][NH:31][CH2:30][CH:29]3[C:33]=2[CH:34]=1>C(#N)C>[CH2:16]([NH:18][C:19](=[O:20])[O-:21])[CH3:17].[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:22][C:23]2[C:24]([Cl:36])=[CH:25][C:26]3[CH:27]([CH3:35])[CH:28]4[CH2:32][NH:31][CH2:30][CH:29]4[C:33]=3[CH:34]=2)=[CH:4][CH:3]=1
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Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 86602845N-Ethylcarbamate 5-hydroxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Produkt 1

HCID 86602847N-Ethylcarbamate 5-(4-fluorobenzyloxy)-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

4-Fluorobenzyl bromide (23 μL, 0.19 mmol) and potassium carbonate (100 mg, 0.78 mmol) were added to a solution of N-ethylcarbamate-5-hydroxy-6-chloro-8-methyl-1,2,3,3a,8,8a-hexahydroindeno[1,2-c]pyrrole (from Example 5, Step A) (46 mg, 0.16 mmol) in acetonitrile (3 mL), and stirred overnight at 80° C. The reaction was cooled to room temperature, concentrated by rotary evaporation and taken up in H2O (5 mL). The product was extracted with EtOAc (3×10 mL). The combined organic extracts were dried over MgSO4 and concentrated to afford the subtitle compound, which was used without further purification. MS calculated for C22H23ClFNO3+H: 404, observed: 404.

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated by rotary evaporation
  3. extractionThe product was extracted with EtOAc (3×10 mL)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f14bca2b2b814605872e5ccefa090405
Quelldatensatz
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08232311B2

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