Benzyloxyamine hydrochloride → hexahydro-1-[(phenylmethoxy) imino]-2,6-methano-1H-pyrrolizine
Reaktionsgleichung
[C:1]1(=O)[CH:8]2[N:4]3[CH2:5][CH:6]([CH2:9][CH:2]1[CH2:3]3)[CH2:7]2.Cl.[CH2:12]([O:19][NH2:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>N1C=CC=CC=1.C(O)C>[C:13]1([CH2:12][O:19][N:20]=[C:1]2[CH:8]3[N:4]4[CH2:5][CH:6]([CH2:9][CH:2]2[CH2:3]4)[CH2:7]3)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
Hexahydro-2,6-methano-1H-pyrrolizin-1-one (N. Speckamp, Tetrahedron, 27, 3143 (1971)), 1.45 g, 11.0 mmol, was dissolved in a 1:1 solution of pyridine/ethanol (20 mL). O-Benzyl hydroxylamine hydrochloride (1.85 g, 11.6 mmol) was added and the solution was stirred for 20 hours at room temperature. Removal of the solvents in vacuo afforded a solid which was purified by chromatography on silica gel eluting with 10% MeOH (NH3)/CHCl3 to give hexahydro-1-[(phenylmethoxy) imino]-2,6-methano-1H-pyrrolizine.