[NH2:1][C@H:2]1[C@H:6]([CH3:7])[CH2:5][N:4]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:3]1.C(N(CC)CC)C.[C:22]([O:26][C:27](ON=C(C1C=CC=CC=1)C#N)=[O:28])([CH3:25])([CH3:24])[CH3:23]>O1CCOCC1>[NH3:1].[CH2:8]([N:4]1[CH2:5][C@@H:6]([CH3:7])[C@H:2]([NH:1][C:27]([O:26][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:28])[CH2:3]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1
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.
Wird geladen…
