[BH4-].[Na+].[CH3:3][C:4]1([CH3:15])[CH2:9][C:8](=[O:10])[CH2:7][CH2:6][CH:5]1[C:11]([O:13][CH3:14])=[O:12].Cl>C(O)C>[OH:10][CH:8]1[CH2:7][CH2:6][CH:5]([C:11]([O:13][CH3:14])=[O:12])[C:4]([CH3:15])([CH3:3])[CH2:9]1Sodium borohydride (1.85 g, 48.9 mmol) was added to a solution of methyl 2,2-dimethyl-4-oxocyclohexanecarboxylate (3.0 g, 16.3 mmol) in ethanol (65 mL) at −20° C. The solution was stirred at −20° C. for 2 hours. Aqueous hydrochloric acid (1M) was added drop wise and the mixture was extracted with dichloromethane (3×). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford methyl 4-hydroxy-2,2-dimethylcyclohexanecarboxylate. 1H NMR (500 MHz, DMSO-d6) δ 3.70-3.58 (m, 1H), 3.54 (s, 3H), 2.16-2.11 (m, 1H), 1.73-1.68 (m, 1H), 1.65-1.48 (m, 4H), 1.07-0.99 (m, 1H), 0.91 (s, 6H).
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