Trifluoroacetic acid → rel-(3aR,6aR)-Methyl 2-benzylhexahydrocyclopenta[c]pyrrole-3a(1H)-carboxylate

HRID 1917330

Reaktionsgleichung

Reaktionsgleichung von HRID 1917330
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]([C:12]1[CH2:16][CH2:15][CH2:14][CH:13]=1)=[O:11].[CH2:17]([N:24]([CH2:30]OC)[CH2:25][Si](C)(C)C)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>ClCCl>[CH3:8][O:9][C:10]([C@:12]12[CH2:16][CH2:15][CH2:14][C@H:13]1[CH2:30][N:24]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:25]2)=[O:11]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 549129Methyl cyclopent-1-ene-1-carboxylate

Produkt 1

HCID 1515514rel-(3aR,6aR)-Methyl 2-benzylhexahydrocyclopenta[c]pyrrole-3a(1H)-carboxylateAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A catalytic amount of trifluoroacetic acid was added to a solution of 1-cyclopentene-1-carboxylic acid methyl ester (2.52 g, 20.0 mmol) and N-benzyl-N-(methoxymethyl)-N-trimethylsilylmethylamine (5.00 g, 21.1 mmol) in dichloromethane (40 mL) at room temperature, and the mixture was heated with stirring at room temperature for 15.5 hours. The reaction solution was diluted with dichloromethane (100 mL) and washed with a saturated sodium bicarbonate solution (80 mL). The washed aqueous layer was further extracted with dichloromethane (50 mL). The organic layers were combined and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5→90:10→80:20) to give 4.28 g (83%) of the title compound as a colorless transparent oil.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. washwashed with a saturated sodium bicarbonate solution (80 mL)
  3. extractionThe washed aqueous layer was further extracted with dichloromethane (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5→90:10→80:20)

Quellen und Nachweise

ORD-Eintrag
ord-0be8207185c648c4ab86050b9ee72355
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618094B2

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