Reaktion #90909

Reaktionsgleichung

N-Benzyl-1-methoxy-N-[(trimethylsilyl)-methyl]methanamine

Trifluoroacetic acid

(1E)-2-(3,5-dichlorophenyl)-3,3,3-trifluoroprop-1-en-1-yl phenyl sulfoxide

N-Benzyl-1-methoxy-N-[(trimethylsilyl)methyl]methanamine

→

1-benzyl-3-(3,5-dichlorophenyl)-4-(phenylsulfonyl)-3-(trifluoromethyl)-pyrrolidine

Ausbeute 83.0%

Lösungsmittel

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITthe reaction left
2. 2
   SonstigeThe solvents of the reaction mixture were removed
3. 3
   FiltrationThe formed crystals were filtered off
4. 4
   Sonstigewas obtained

Vorschrift

Trifluoroacetic acid (38 μL, 513 μmol) was added to (1E)-2-(3,5-dichlorophenyl)-3,3,3-trifluoroprop-1-en-1-yl phenyl sulfoxide (4.00 g, 98% purity, 10.3 mmol) in toluene (20 mL). N-Benzyl-1-methoxy-N-[(trimethylsilyl)methyl]methanamine (3.65 g, 15.4 mmol) in toluene (18 mL) was added at room temperature over two hours. After two more hours additional N-Benzyl-1-methoxy-N-[(trimethylsilyl)-methyl]methanamine (0.2 eq.) was added and the reaction left stirring for another hour. The solvents of the reaction mixture were removed and the crude product was taken up in n-heptane. The formed crystals were filtered off. 1-Benzyl-3-(3,5-dichlorophenyl)-4-(phenylsulfinyl)-3-(trifluoromethyl)-pyrrolidinium chloride (4.40 g, >99% purity, 83% yield, E/Z [not assigned]=53/47) was obtained.

Quelle