[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][CH2:4][CH:5]1[CH2:10][CH:9]([CH2:11][OH:12])[CH2:8][CH2:7][N:6]1[C:13]([O:15][CH3:16])=[O:14].[Na].[OH2:20]>C(Cl)(Cl)(Cl)Cl.C(#N)C.C(Cl)Cl.[Ru](Cl)(Cl)Cl>[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][CH2:4][CH:5]1[CH2:10][CH:9]([C:11]([OH:20])=[O:12])[CH2:8][CH2:7][N:6]1[C:13]([O:15][CH3:16])=[O:14]Methyl 2-(3,3-dimethylbutyl)-4-(hydroxymethyl)piperidine-1-carboxylate (2.44 g, 9.49 mmol) was dissolved in CCl4 (20 mL) and acetonitrile (20 mL). Sodium periodiate (6.09 g, 28.5 mmol) was added followed by water (30 mL) and ruthenium (III) chloride (43 mg, 0.21 mmol). The resulting suspension was stirred at room temperature for 3 h 50 min. The reaction mixture was diluted with DCM (100 mL) and water (100 mL). The aqueous layer was extracted with DCM (×3) and the combined organic phase passed through a phase separator and evaporated to yield crude 2-(3,3-dimethylbutyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (2.42 g, 94%) as a black solid. MS m/z 272 (M+H)+
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