HCID 131718275, compound → HCID 131718276, compound

Temperature

80 °C

Methyl (1S, 4aS, 7S, 7aR)-1-[1-(ethoxy)ethoxy]-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4carboxylate (1.0 g, 0.0035 mol) obtained in Example 4 was dissolved in 20 ml of ethanol suspending nickel chloride (1.14 g), and 10 ml 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 ml of ethyl acetate, washed with water (50 ml×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 ml of tetrahydrofuran without purification and was stirred at room temperature for 2 hours after the addition of 10 ml of 2N hydrochloric acid solution. After the reaction solution was neutralized by adding 50 ml of saturated sodium bicarbonate solution, it was extracted by ethyl acetate (50 ml×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-7methylcyclopenta[c]pyran-4-carboxylate had the following physicochemical properties:

1. additionwas added
2. temperatureunder heat-reflux
3. filtrationThe reaction mixture solution was filtered by a celite
4. concentrationwas once concentrated under a reduced pressure
5. dissolutionThe residual matter was dissolved in 100 ml of ethyl acetate
6. washwashed with water (50 ml×3)
7. dry with materialdried by the addition of magnesium sulfate
8. distillationthe solvent was distilled off under a reduced pressure
9. dissolutionThe residual matter was dissolved in 30 ml of tetrahydrofuran without purification
10. stirringwas stirred at room temperature for 2 hours
11. additionafter the addition of 10 ml of 2N hydrochloric acid solution
12. additionby adding 50 ml of saturated sodium bicarbonate solution, it
13. extractionwas extracted by ethyl acetate (50 ml×3)
14. dry with materialit was dried by the addition of magnesium sulfate
15. filtrationfiltered
16. concentrationconcentrated under a reduced pressure
17. customThe residual matter was purified by chromatography
18. customthe solvent of the fraction obtained from hexane
19. distillationether=7:3 eluent was distilled off
20. customA colorless oily substance was thus obtained

ORD record

ord-23700b9e7a474d1c8854fdb21eab00dc

Source dataset

uspto-grants-1994_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05374653