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

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Reaktionsgleichung

F[C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.CCN(CC)CC.S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH3:33][C@H:34]1[CH2:38][CH2:37][CH2:36][NH:35]1>CC#N>[CH3:33][C@H:34]1[CH2:38][CH2:37][CH2:36][N:35]1[C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a solution of 5-fluoro-2-nitrobenzotrifluoride (2.0 g, 9.56 mmol) in CH3CN (20 mL) was added Et3N (2.41 g, 23.90 mmol) followed by the addition of (S)-2-methylpyrrolidine tosylate (3.18 g, 12.43 mmol). The reaction was stirred at 80° C. overnight. The reaction was then quenched with water and the aqueous layer was extracted with DCM. The combined organics were washed with 1N HCl, dried over MgSO4, filtered and concentrated to give (S)-2-methyl-1-(4-nitro-3-(trifluoromethyl) phenyl) pyrrolidine (2.45 g, 94% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.11 (d, J=9.1 Hz, 1H), 6.88 (s, 1H), 6.85 (d, J=2.6 Hz, 1H), 4.17-4.13 (m, 1H), 3.59-3.54 (m, 1H), 3.33-3.28 (m, 1H), 2.14-2.00 (m, 3H), 1.80-1.71 (m, 1H), 1.14 (d, J=6.3 Hz, 3H). LC/MS: m/z 275.3 (M+H)+ at 1.98 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Aufarbeitung

customThe reaction was then quenched with water
extractionthe aqueous layer was extracted with DCM
washThe combined organics were washed with 1N HCl
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-83777800a67e494dbcee40e652087c2a
Quelldatensatz: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08354427B2

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