m-Chloroperbenzoic acid → (S)-1-{(3S,3aS,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-indene-3-yl}ethyl formate

Participants

Reaction Steps

Under a nitrogen atmosphere, a solution of (S)-2-{(3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-indene-3-yl}propanal (Compound 15: 1.85 g, 8.797 mmol) in methylene chloride (30 ml) was cooled in an ice bath, and sodium dihydrogen phosphate dihydrate (6.86 g, 43.99 mmol) was added thereto. Meta-chloroperbenzoic acid (3.50 g, 13.2 mmol, calculated as 65%) was added thereto over 10 minutes. The reaction solution was stirred in the ice bath for 30 minutes, and at 17° C. to 21° C. for 12.5 hours. The reaction mixture was transferred to a separatory funnel such that insoluble matters were not included therein (the reaction vessel was washed with ethyl acetate), and water (40 ml) and ethyl acetate were added thereto. The aqueous layer was extracted twice with ethyl acetate. The combined organic layer was washed with saturated aqueous sodium thiosulfate solution (45 ml), saturated aqueous sodium hydrogen carbonate solution (25 ml) and with saturated brine (50 ml), and dried over sodium sulfate, followed by evaporation under reduced pressure. The crude product (2.41 g) was purified by flash column chromatography to obtain (S)-1-{(3S,3aS,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-indene-3-yl}ethyl formate (1.80 g).

Provenance & Evidence