[N:1]([CH2:4][C:5]1([CH3:21])[CH2:20][CH2:19][CH2:18][C:7]2([O:11][C:10](=[O:12])[N:9]([CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:8]2)[CH2:6]1)=[N+]=[N-].[BH4-].[Na+]>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[NH2:1][CH2:4][C:5]1([CH3:21])[CH2:20][CH2:19][CH2:18][C:7]2([O:11][C:10](=[O:12])[N:9]([CH2:13][C:14]([CH3:16])([CH3:17])[CH3:15])[CH2:8]2)[CH2:6]1To a light green 0° C. solution of 7-(azidomethyl)-7-methyl-3-neopentyl-1-oxa-3-azaspiro[4.5]decan-2-one (10.0 g, 34.0 mmol) and nickel (II) chloride hexahydrate (8.07 g, 34.0 mmol) in MeOH (226 mL) was added sodium borohydride (1.93 g, 51.0 mmol) in six portions. The reaction quickly became black and was allowed to stir at 0° C. for 3 h. The reaction mixture was concentrated and partitioned between 1 N NaOH (350 mL) and EtOAc (350 mL). The biphasic mixture was filtered through celite, and the layers were separated. The aqueous layer was extracted with EtOAc (2×150 mL). The combined organics were dried over MgSO4, filtered, and concentrated to afford the title compound (8.65 g, 90% crude yield) as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ 3.33 (dd, J=8.53, 13.80 Hz, 2H), 3.06 (d, J=14.05 Hz, 1H), 2.93 (d, J=14.05 Hz, 1H), 2.43 (s, 2H), 1.99 (dt, J=1.76, 13.55 Hz, 1H), 1.89 (dt, J=3.48, 13.87 Hz, 1H), 1.69 (d, J=14.05 Hz, 1H), 1.57 (dt, J=4.11, 13.87 Hz, 1H), 1.29-1.47 (m, 3H), 1.15-1.28 (m, 1H), 1.08 (s, 3H), 0.96 (s, 9H).
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