Triphenylphosphine → HCID 10220866, compound

Participants

Reaction Steps

To a solution of (R) -1-azido-7-chloro-4,4a, 9,10-tetrahydro-4a-methyl-2 (3H) -phenanthreneone (0.210 g, 0.730 mmol) in tetrahydrofuran (8 mL) and water (1 mL) was added triphenylphosphine (0.325 g, 1.24 mmol). After refluxing for 20 minutes the mixture was cooled and the tetrahydrofuran evaporated. The resulting system was diluted with toluene (8 mL) and refluxed for 16 hours. The mixture was evaporated and the residue was purified by chromatography (Chromatotron, Harrison Research, Palo Alto, Calif.) (15% ethyl acetate/hexane) twice to give 42 mg (22%) of the title amine as a white powder. IR (KBr) 1648 (CO)cm-1 ; 1H NMR (300 MHz, CDCl3) δ7.23 (s, 2H), 7.15 (s, 1H), 2.98-3.07 (m, 1H), 2.75-2.93 (m, 3H), 2.48-2.67 (m, 2H), 2.36-2.47 (m, 1H), 2.05-2.16 (m, 1H), 1.49 (s,3H); MS (FD)m/z 261 (M+); UV λmaxEtOH (nm) (ε) 203 (20595), 294 (6036).

Provenance & Evidence