Imidazole → (3aR,4R,5R,6aS)-5-Benzoyloxy-4-[(t-butyldiphenylsiloxy)methyl]hexahydro-2H-cyclopenta[b]furan-2-one

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Reaction Steps

To a solution of 2 (2.40 g, 8.8 mmol), 4-(dimethylamino)pyridine (100 mg, 0.82 mmol), and imidazole (1.00 g, 14.7 mmol) in methylene chloride (35 mL) was added dropwise t-butyldiphenylchlorosilane (2.85 g, 10.4 mmol). After stirring overnight, the mixture was added to saturated ammonium chloride (40 mL), extracted with ethyl acetate (3×40 mL), dried (magnesium sulfate), filtered, concentrated, and chromatographed on a 14 cm tall×53 mm diameter silica gel eluting with 30% ethyl acetate in hexane to afford 3 (3.776 g, 83%).

Provenance & Evidence