Water → trans-4-(Boc-amino)cyclohexyl methanesulfonate

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To a solution of tert-butyl N-(4-hydroxycyclohexyl)carbamate (3.8 g, 17.65 mmol, 1.00 equiv) and triethylamine (3.9 g, 38.54 mmol, 2.20 equiv) in dichloromethane (40 mL) was added methanesulfonyl chloride (2.43 g, 21.21 mmol, 1.21 equiv) dropwise with stirring at 0° C. The reaction mixture was stirred overnight at room temperature. Water (50 mL) was added to quench the reaction. The resulting mixture was extracted with 3×50 mL of dichloromethane. The combined organic layers was washed with 2×200 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 3.0 g (58%) of tert-butyl N-[4-(methanesulfonyloxy)cyclohexyl]carbamate as a white solid.

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