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Triethylamine (2.4 mL, 17 mmol) was added to a solution of 1,4-dioxaspiro[4,5]decan-9-ol (884 mg, 5.59 mmol) in dichloromethane (22 mL) under a nitrogen atmosphere. The solution was cooled to 0° C. in an ice bath. Methanesulfonyl chloride (0.87 mL, 11.2 mmol) was added and the reaction stirred for 4 h while warming up to room temperature. Water was added and the mixture was extracted with dichloromethane (2×). The combined organic layers were washed with brine (1×), dried with magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0 to 100% EtOAc/hexane) to afford 1,4-dioxaspiro[4.5]dec-8-yl methanesulfonate as a light yellow oil. 1H NMR (500 MHz, DMSO-d6) δ 4.81-4.68 (m, 1H), 3.91-3.78 (m, 4H), 3.16 (s, 3H), 1.87 (ddd, J=4.2, 8.1, 16.6, 2H), 1.82-1.71 (m, 2H), 1.67 (ddd, J=4.3, 7.9, 12.3, 2H), 1.58 (ddd, J=4.8, 8.7, 13.3, 2H).

1. temperaturewhile warming up to room temperature
2. extractionthe mixture was extracted with dichloromethane (2×)
3. washThe combined organic layers were washed with brine (1×)
4. dry with materialdried with magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by column chromatography on silica gel (0 to 100% EtOAc/hexane)