Reaktion #1992096

Reaktionsgleichung

N-benzyl-N-(cyanomethyl)-N-[(trimethylsilyl)methyl]amine

methyl atropate

acetonitrile

→

methyl 3-phenyl-1-(phenylmethyl)-3-pyrrolidinecarboxylate

Ausbeute 41.1%

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered through celite
2. 2
   SonstigeConcentration of the filtrate gave an oil which
3. 3
   Sonstigewas chromatographed on silica gel
4. 4
   Wascheneluting with an 80:20 chloroform

Vorschrift

A suspension of 53.4 g (0.23 mol) of N-benzyl-N-(cyanomethyl)-N-[(trimethylsilyl)methyl]amine (J. Org. Chem., 50, 4006 (1985)), 41.2 g (0.25 mol) of methyl atropate, 32.2 g (0.25 mol) of silver fluoride and 1 l of acetonitrile was stirred overnight at room temperature in the dark. The mixture was diluted with chloroform and filtered through celite. Concentration of the filtrate gave an oil which was chromatographed on silica gel, eluting with an 80:20 chloroform:ethyl acetate mixture, to give 27.9 g of methyl 3-phenyl-1-(phenylmethyl)-3-pyrrolidinecarboxylate.

Quelle