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According to Tetrahedron Lett., 1979, 17, 1503, to a stirred solution of phenylmagnesium chloride (0.753 mL, 1.51 mmol) and copper (I) iodide (0.0191 g, 0.100 mmol) in THF (3 mL) at -300C was added tert-butyl 7-oxa-3-aza- bicyclo[4.1.0]heptane-3-carboxylate (0.200 g, 1.00 mmol) in THF (1 mL) . The mixture was allowed to warm to room temperature and was stirred for 16 h. It was then quenched with saturated aqueous ammonium chloride and the mixture was extracted with AcOEt. The combined organic layers were dried (sodium sulfate) , filtered, and concentrated in vacuo to give tert-butyl 3-hydroxy-4-phenylpiperidine-l-carboxylate (0.261 g, 94%) as an oil: 1H NMR (400 MHz, DMSO-d6) delta 1-49 (s, 9H), 1.76 (m, 3H), 2.50-2.78 (m, 3H), 3.70 (m, IH), 4.30 (bd, IH), 7.30 (m, 5H).
(s) From (3RS,4SR)-4-phenyl-piperidin-3-ol [J. A. Gauthier et al., U.S. Pat. No. 4,132,710] by introduction of the BOC group there was obtained tert-butyl (3RS,4SR)-3-hydroxy-4-phenyl-piperidine-1-carboxylate as a colourless solid; m.p.: 134-134.5 C. Subsequent alkylation with 2-bromomethylnaphthalene gave tert-butyl (3RS,4SR)-3-(naphthalen-2-ylmethoxy)-4-phenyl-piperidine-1-carboxylate as a colourless solid; MS: 417 (M)+.
3
[ 1000931-04-3 ]
tert-butyl (3RS,4RS)-4-cyclohexyl-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
rhodium(5%)-aluminium oxide; In methanol;
(j) A solution of 4.0 g tert-butyl (13.8 mmol) of <strong>[1000931-04-3]tert-butyl (3RS,4RS)-3-hydroxy-4-phenyl-piperidine-1-carboxylate</strong> in 100 ml of methanol was hydrogenated at 150 bar at 100 C. for 18 hours using a rhodium(5%)-aluminium oxide catalyst. For the working up, the catalyst was filtered off, washed with methanol and the solution obtained was evaporated under reduced pressure. For purification, the residue was chromatographed on silica gel using a 4:1 mixture of hexane and ethyl acetate as the eluent. There were obtained 2.32 g (59% of theory) of tert-butyl (3RS,4RS)-4-cyclohexyl-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate as a colourless solid; MS: 283 (M)+.
(a) From 4-phenyl-piperidin-4-ol there was obtained by elimination 4-phenyl-1,2,3,6-tetrahydro-pyridine as a light yellow oil; MS: 159 (M)+. Subsequent hydroboration gave (3RS,4RS)-4-phenyl-piperidin-3-ol as a colourless solid; MS: 177 (M)+. Introduction of the BOC group yielded tert-butyl (3RS,4RS)-3-hydroxy-4-phenyl-piperidine-1-carboxylate as a colourless solid; MS: 277 (M)+.
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