[CH2:1]([N:8]1[CH2:15][CH:14]2[O:16][CH:10]([CH2:11][N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N#N.[ClH:26]>C(OCC)(=O)C.C(OCC)C>[ClH:26].[CH2:1]([N:8]1[CH2:9][CH:10]2[O:16][CH:14]([CH2:13][N:12]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:11]2)[CH2:15]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1A solution of tert-butyl 7-benzyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (39.5 g, 0.12 mol) in ethyl acetate (200 mL) was cooled to −10° C. under an inert atmosphere (N2). A solution of HCl in diethyl ether (1 M) was added over the course of 1 h, during which time a precipitate formed. After addition was complete, the resulting mixture was stirred for a further 1 h before the crystalline precipitate was collected by filtration and dried in a vacuum oven (40° C., 13.3 Pa (0.1 mmHg)). This gave 42.6 g (100% from the compound of step (iii) above) of the sub-title compound as an off-white crystalline material.
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