Trifluoroacetic acid → (3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carboxylic acid

HRID 906917

Reaktionsgleichung

Reaktionsgleichung von HRID 906917
CO[CH2:3][N:4]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:5][Si](C)(C)C.[Cl:17][C:18]1[CH:19]=[C:20](/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28])[CH:21]=[CH:22][C:23]=1[Cl:24].FC(F)(F)C(O)=O>C1COCC1.CCCCCCC>[CH2:10]([N:4]1[CH2:3][CH:25]([C:20]2[CH:21]=[CH:22][C:23]([Cl:24])=[C:18]([Cl:17])[CH:19]=2)[CH:26]([C:27]([OH:29])=[O:28])[CH2:5]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

6

Edukt 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 6880273,4-Dichlorocinnamic acid

Produkt 1

HCID 16244042(3RS,4SR)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8900HeptaneLösungsmittel

Versuchsvorschrift

To a solution of N-(methoxymethyl)-N-(phenylmethyl)-N-(trimethylsilyl)methylamine (16.87 g, 0.071 mol) and (E)-3-(3,4-Dichloro-phenyl)-acrylic acid (7.71g, 0.036 mol) in THF (50 mL) was added trifluoroacetic acid (0.19 mL, 0.002 mol) at 0° C. The mixture was gradually warmed to room temperature and stirred overnight. It was then diluted with n-heptane (250 mL). The resulted white precipitation was collected and washed with heptane affording 11.6 g (94%) of the title compound as a white solid. ES-MS m/e: 350.2 (M+H+).

Aufarbeitung

  1. customThe resulted white precipitation
  2. customwas collected
  3. washwashed with heptane affording 11.6 g (94%) of the title compound as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-c403eef601ad4e949d731aacf82718e5
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012998B2

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