CC(C)(S([NH:6][C:7]1([CH3:21])[CH2:12][CH2:11][CH:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:9][CH2:8]1)=O)C.[ClH:23]>CO.O1CCOCC1>[ClH:23].[NH2:6][C:7]1([CH3:21])[CH2:12][CH2:11][CH:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])[CH2:9][CH2:8]1To a stirred solution of tert-butyl 4-(1,1-dimethylethylsulfinamido)-4-methylcyclohexylcarbamate (0.2 g, 0.6 mmol) in 100 mL of MeOH was added a saturated solution of HCl (g) in dioxane (0.72 mL). The solution was stirred at room temperature overnight. The solvent was removed under reduced pressure, the residue was triturated with EtOAc (15 mL), then decanted and dried to give tert-butyl 4-amino-4-methylcyclohexylcarbamate hydrochloride (0.1 g, 63%) as a white solid. MS: (M+H)+=229.2. 1H NMR (300 MHz, CD3OD): δ 3.36 (m, 1H), 1.91-1.66 (m, 9H), 1.40 (s, 9H), 1.18 (s, 3H).
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