Br[CH2:2][C:3]1([CH3:19])[CH2:18][CH2:17][CH2:16][C:5]2([O:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:6]2)[CH2:4]1.[N-:20]=[N+:21]=[N-:22].[Na+]>CS(C)=O.O>[N:20]([CH2:2][C:3]1([CH3:19])[CH2:18][CH2:17][CH2:16][C:5]2([O:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:6]2)[CH2:4]1)=[N+:21]=[N-:22]To a solution of 7-(bromomethyl)-7-methyl-3-neopentyl-1-oxa-3-azaspiro[4.5]decan-2-one (11.3 g, 34.1 mmol) in DMSO (171 mL) was added sodium azide (2.89 g, 44.4 mmol). The reaction flask was placed behind a blast shield and heated to 80° C. for 4 days. The temperature was increased to 100° C. After 16 h, additional sodium azide (0.665 g, 10.23 mmol) was added to the reaction. After 19 h, the reaction was cooled to rt and diluted with water (300 mL). The product was extracted into EtOAc (2×300 mL). The combined organics were washed with water (3×400 mL). The organic layer was dried over MgSO4, filtered, and concentrated to provide the title compound (10.0 g, 95% crude yield) as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ 3.33 (q, J=8.53 Hz, 2H), 3.09 (s, 2H), 3.06 (d, J=14.00 Hz, 1H), 2.94 (d, J=14.05 Hz, 1H), 1.96-2.05 (m, 1H), 1.83-1.96 (m, 1H), 1.69 (dt, J=2.04, 14.24 Hz, 1H), 1.59-1.65 (m, 1H), 1.47 (d, J=14.05 Hz, 1H), 1.26-1.44 (m, 3H), 1.15 (s, 3H), 0.97 (s, 9H).
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