Reaktion #1784622

Reaktionsgleichung

O-(perfluorobenzyl)hydroxylamine HCl

1-azatricyclo[3.3.1.13,7]decan-4-one

→

title compound

1-azatricyclo[3.3.1.13,7]decan-4-one O-(pentafluorobenzyl)oxime

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwith warming
2. 2
   workup.DISSOLUTIONto dissolve all solids
3. 3
   SonstigeThe solvent was removed under vacuum
4. 4
   Sonstigethe residue was crystallized from 10% ethanol in ethyl acetate (3 mL)

Vorschrift

Solid O-(perfluorobenzyl)hydroxylamine HCl (167 mg, 0.669 mmol, Aldrich Chemical Co.) was added to a warm solution of 1-azatricyclo[3.3.1.13,7]decan-4-one (102 mg, 0.675 mmol) (prepared as reported in: Becker, D. P. and Flynn, D. L. Synthesis 1992, 1080-1082) in ethanol (1 mL). The mixture was swirled with warming to dissolve all solids. The nearly colorless solution was allowed to cool to room temperature overnight. The solvent was removed under vacuum, and the residue was crystallized from 10% ethanol in ethyl acetate (3 mL) to provide the title compound as hydrochloride salt. 1H NMR (300 MHz, CD3OD) δ 1.87-2.06 (m, 2 H), 2.22 (q, J=3 Hz, 1 H), 2.24-2.37 (m, 2 H), 2.83 (s, 1H), 3.30, (m, 1H), 3.43-3.57 (m, 2 H), 3.64 (s, 2 H), 3.66-3.78 (m, 2 H), 5.15-5.24 ppm (m, 2 H); MS (DCI/NH3) m/z 347 (M+H)+; Anal. C16H15N2OF5—HCl requires C, 50.21; H, 4.21; N, 7.32. Found C, 50.20; H, 3.99; N, 7.22.

Quelle