Neopentyl glycol → Simvastatin

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A mixture of simvastatin phenylboronate (5.22 g, 0.010 mol), toluene (31 mL), and neopentyl glycol (1.11 g, 0.0107 mol) was heated under a nitrogen atmosphere at 77 to 79° C. for 1 hour and 40 minutes. The solution was concentrated under reduced pressure at a bath temperature of 60° C. to a final volume of 5 mL and n-heptane (160 mL) was added at a temperature of 50-60° C. The crude simvastatin was filtered and washed with heptane to provide 3.17 g (76%) of simvastatin. By appropriate manipulation of the conditions and reagents, compounds such as the compactin analogue of simvastatin may be prepared.

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