Water → Methyl 3-hydroxycyclohexane-1-carboxylate

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3-oxo-1-cyclohexanecarboxylic acid methyl ester (1.1 g, 7.04 mmol) was dissolved in methanol (25 ml) and cooled to 0° C. under N2. Sodium borohydride (0.550 g, 14.54 mmol) was added in portions and the resulting solution stirred at 0° C. for 2 h. The solution was then diluted by the dropwise addition of water, followed by EtOAc (100 mL). The aqueous phase was separated and extracted with EtOAc (2×50 ml). The combined organic layers were washed with brine, dried over sodium sulphate, and concentrated in vacuo to give the title compound. TLC: 40% EtOAc/hexanes, high Rf: 0.4, low Rf: 0.3.

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