Hydrochloric Acid → (2RS,5SR)-5-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-2H-tetrazole

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Reaktionsgleichung

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:11]([C:23]#[N:24])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[N-:25]=[N+:26]=[N-:27].[Na+].Cl.C(N(CC)CC)C.Cl>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[N:12]([S:13]([C:16]3[CH:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=3)(=[O:15])=[O:14])[CH:11]([C:23]3[N:25]=[N:26][NH:27][N:24]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

To a stirred solution of (2RS,5SR)-5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carbonitrile (0.70 g, 2.03 mmol) in DMF (25 ml) was added at room temperature sodium azide (0.40 g, 6.10 mmol) and triethylamine hydrochloride (0.42 g, 3.05 mmol) and the reaction mixture was stirred at 120° C. for 6 h. The mixture was poured in water (100 ml), acidified (2 N HCl) and the formed solid was collected to give (2RS,5SR)-5-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-2H-tetrazole (0.73 g, yield 93%) as an off-white solid, m.p. 150° C.

Aufarbeitung

customthe formed solid was collected

Quellen und Nachweise

ORD-Eintrag: ord-6e854b763234477bbe474b6e366dae58
Quelldatensatz: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06589978B2

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