[C:1]([C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])#[N:2].Cl.[NH2:17][OH:18].C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[NH2:2]/[C:1](=[N:17]\[OH:18])/[C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]A solution of tert-butyl (2S)-2-cyano-1-piperidinecarboxylate (13.10 g) [see Preparation 3] in methanol (500 ml) was added to a solution of hydroxylamine hydrochloride (21.6 g) and sodium carbonate (33.0 g) in water (600 ml). The reaction mixture was warmed to the reflux temperature and stirred for 8 hours after which time the methanol was removed under reduced pressure and the product extracted from the aqueous layer with ethyl acetate (3×500 ml). The combined organic layers were washed with water (500 ml), dried over magnesium sulphate and the solvent removed under reduced pressure to afford tert-butyl (Z)-(2S)-2-[amino(hydroxyimino)methyl]-1-piperidinecarboxylate (14.1 g) as a white solid.
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