[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH:7]1[CH2:12][CH2:11][CH:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:1][S:2]([O:6][CH:7]1[CH2:8][CH2:9][CH:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12]1)(=[O:4])=[O:3]
Methanesulfonyl chloride (0.53 mL, 6.80 mmol) was added to a −20° C. solution of tert-butyl 4-hydroxycyclohexanecarboxylate (1.05 g, 5.25 mmol) and triethylamine (1.46 mL, 10.5 mmol) in dichloromethane (21 mL). The reaction was stirred for 2 hours, then saturated aqueous sodium bicarbonate was added and the mixture was extracted with EtOAc (3×). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford tert-butyl 4-[(methylsulfonyl)oxy]cyclohexanecarboxylate. 1H NMR (500 MHz, CDCl3) δ 4.96-4.55 (m, 1H), 3.00 (s, 3H), 2.23-2.12 (m, 2H), 2.03-1.98 (m, 2H), 1.93-1.81 (m, 1H), 1.79-1.66 (m, 1H), 1.66-1.48 (m, 3H), 1.42 (s, 9H).
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