4-Toluenesulfonyl chloride → (3S,5R)-5-Methyl-3-(toluene-4-sulfonyloxymethyl)nonanoic acid tert-butyl ester

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Reaction Steps

To alcohol 140 (6.14 mmol) in 30 mL CH2Cl2 at 0° C. was added DMAP (0.1 g), p-toluenesulfonyl chloride (1.37 g, 7.2 mmol), and then triethylamine (1.8 mL, 13 mmol) was added quickly dropwise. The mixture was warmed immediately to ambient temperature following addition and stirred overnight, and did not proceed to completion. The mixture was partitioned between Et2O and 1N HCl (aq), the phases were separated, and the organic phase washed with sat. NaHCO3 (aq), dried (MgSO4), and concentrated to provide tosylate 141. The product was used without further purification.

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