Potassium Carbonate → (S)-2-{(3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-indene-3-yl}propanal

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Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, a solution of (1R,3aR,4S,7aR)-octahydro-1-{(S)-1-hydroxypropane-2-yl}-7a-methyl-1H-indene-4-ol (Compound 14: 2.05 g, 9.659 mmol) synthesized according to the method described in J. Org. Chem. 1986, 51, 1264-1269, 4-acetamide-2,2,6,6-tetramethyl-1-piperidinyloxy free radical (155 mg, 0.7244 mmol) and tetra-n-butylammonium chloride (134 mg, 0.4830 mmol) in methylene chloride (90 ml) was cooled in an ice bath, and 0.5 M sodium hydrogen carbonate (45 ml) and 0.05 M potassium carbonate (45 ml) were added thereto. N-chlorosuccinimide (3.87 g, 28.98 mmol) was added thereto over 10 minutes. The reaction solution was stirred in the ice bath for 1.5 hours, at 10° C. to 18° C. for 4.5 hours, at 5° C. for 11.5 hours, and then at 10° C. to 15° C. for 4.25 hours. After adding saturated aqueous sodium thiosulfate solution (15 ml), the resulting mixture was stirred at 15° C. for 20 minutes. The resulting mixture was extracted 3 times with methylene chloride. The combined organic layer was dried over sodium sulfate, and evaporated under reduced pressure. The crude product (2.90 g) was purified by flash column chromatography to obtain (S)-2-{(3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-indene-3-yl}propanal (1.87 g).

Provenance & Evidence