HCID 131718275, compound → HCID 131718276, compound

Participants

Reaction Conditions

Reaction Steps

Methyl (1S, 4aS, 7S, 7aR)-1-[1-(ethoxy)ethoxy]-7-methyl-1, 4a, 5, 6, 7, 7a-hexahydrocyclopenta[c]pyran-4-carboxylate (1.0 g, 0.0035 mol) obtained in Example 4 was dissolved in 20 mι of ethanol suspending nickel chloride (1.14 g), and 10 mι of an ethanol solution of sodium boron hydride (830 mg, 0.021 mol) was added. Thereafter, the reaction solution was stirred at 80° C. for 3 hours under heat-reflux. The reaction mixture solution was filtered by a celite, and was once concentrated under a reduced pressure. The residual matter was dissolved in 100 mι of ethyl acetate, washed with water (50 mι×3) and dried by the addition of magnesium sulfate. The residual matter was further filtered, and the solvent was distilled off under a reduced pressure. The residual matter was dissolved in 30 mι of tetrahydrofuran without purification and was stirred at room temperature for 2 hours after the addition of 10 mι of 2N hydrochloric acid solution. After the reaction solution was neutralized by adding 50 mι of saturated sodium bicarbonate solution, it was extracted by ethyl acetate (50 mι×3). After the organic layer was Joined, it was dried by the addition of magnesium sulfate, filtered, and then concentrated under a reduced pressure. The residual matter was purified by chromatography using silica gel, and the solvent of the fraction obtained from hexane:ether=7:3 eluent was distilled off. A colorless oily substance was thus obtained, i.e., methyl (4aS, 7S, 7aR)-1, 3, 4, 4a, 5, 6, 7, 7a-octahydro-1-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylate (480 mg, yield=63.7%). This methyl (4aS, 7S, 7aR)-1, 3, 4, 4a, 5, 6, 7, 7a-octahydro-1-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylate had the following physicochemical properties:

Provenance & Evidence