[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([OH:16])([CH2:14][NH2:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:24](Cl)(Cl)=[O:25].C1(C)C=CC=CC=1>C(#N)C.C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([O:16][C:24](=[O:25])[NH:15][CH2:14]2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1To a solution of crude 1-benzyl-4-hydroxy-4-aminomethyl piperidine, as described above in Step A, (˜3.1 gm, 12 mmol) in acetonitrile (50 mL) containing triethyl amine (5.7 mL, 42 mmol) cooled in an ice bath was added in 1 mL portions 20% phosgene/toluene (9 mL) over a three hour period. The reaction mixture was stirred at ambient temp. for 15 hours and diluted with ethyl acetate. This solution was washed with water (2×) and the organic layer dried (anhyd. sodium sulfate), filtered, and the solvent removed under vacuum. The residue was triturated with diethyl ether and the title compound collected by filtration as a white solid, mp: 159-161° C.
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