Triethylamine → (S)-2-methyl-1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidine

HRID 383396

Reaktionsgleichung

Reaktionsgleichung von HRID 383396
S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH3:12][C@H:13]1[CH2:17][CH2:16][CH2:15][NH:14]1.F[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[C:21]([C:28]([F:31])([F:30])[F:29])[CH:20]=1.C(N(CC)CC)C>C(#N)C>[CH3:12][C@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[C:21]([C:28]([F:29])([F:31])[F:30])[CH:20]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 2230945-Fluoro-2-nitrobenzotrifluorideHCID 44118660(S)-2-Methylpyrrolidine 4-methylbenzenesulfonate

Produkt 1

HCID 59395009(S)-2-methyl-1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidineAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
82 °C

Versuchsvorschrift

To a solution of (S)-2-methylpyrrolidine tosylate (10.6 g, 41.2 mmol) in acetonitrile (85 mL) was added 4-fluoro-1-nitro-2-(trifluoromethyl)benzene (6.6 g, 31.7 mmol) dropwise and followed by triethylamine (11.0 mL, 79.3 mmol) dropwise. The reaction was heated at 82° C. for 16 h. The reaction was quenched with water and extracted with ethyl acetate. The organic layer was washed with 1N HCl, then dried over Na2SO4 and concentrated in vacuo to yield (S)-2-methyl-1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidine (8.7 g, quantitative yield). LC/MS m/z 275.3 [M+H]+.

Aufarbeitung

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with 1N HCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5026c783114c4fe5bc0d8d53c1c77604
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367660B2

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