Reaktion #667747

Reaktionsgleichung

trans-3-amino-1-benzyl-4-methylpyrrolidine

triethylamine

t-butoxycarbonyloxyimino-2-phenylacetonitrile

→

title compound

Ausbeute 171.7%

1-Benzyl-trans-3-t-butoxycarbonylamino-4-methylpyrrolidine

Ausbeute 171.7%

ammonia

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter stirring for 3 hours
2. 2
   Extraktionextracted with ether
3. 3
   WaschenThe organic layer was washed 1N aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution successively
4. 4
   Trocknendried over anhydrous sodium sulfate
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue was purified by silica-gel column chromatography
7. 7
   Wascheneluting with benzene to chloroform

Vorschrift

To a solution of trans-3-amino-1-benzyl-4-methylpyrrolidine hydrocarbonate (4.0 g) and triethylamine (3.2 g) in 50% aqueous dioxane (50 ml) was added t-butoxycarbonyloxyimino-2-phenylacetonitrile (Boc-ON, 5.8 g) with stirring at room temperature. After stirring for 3 hours, the reaction mixture was poured into ice-water and extracted with ether. The organic layer was washed 1N aqueous sodium hydroxide solution and saturated aqueous sodium chloride solution successively, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica-gel column chromatography eluting with benzene to chloroform:methanol:concentrated aqueous ammonia (10:10:1) to give the title compound (5.24 g). Recrystallization from hexane gave colorless needles (5.04 g), mp 79°-80° C.

Quelle