Methanol → HCID 11008194, compound

Methyl (4aS, 7R, 7aR)-1,4a,5,6,7,7a-hexahydro-1-hydroxy-7-methylcyclopenta[c]pyran-4-carboxylate (300 mg, 0.0014 mol) and sodium boron hydride (270 mg, 0,007 mol) were dissolved in 8 ml of tetrahydrofuran, and while the reaction mixture was refluxed at80° C., 1.5 ml of methanol was added dropwise in the course of 1 hour. The reaction mixture was stirred at the same temperature for 5 hours, and 10 ml of a saturated ammonium chloride solution wad added. The reaction mixture was once concentrated under a reduced pressure, and extraction was made with ethyl acetate (50 ml×2). The organic layers were joined, dried by adding magnesium sulfate, filtered and thereafter concentrated under a reduced pressure. The residual substance was purified by chromatography using silica gel, and the solvent of the fraction obtained from ether:ethyl acetate=1:1 eluent was distilled, and a colorless oily substance was obtained, i.e., 2-[(1R, 2R, 3S)-2-(hydroxymethyl)-3-methylcyclopent-1-yl]ethan-1-ol (169 mg, yield=63.8%). This 2-[(1R, 2R, 3S)-2-(hydroxymethyl)-3-methylcyclopent-1-yl]ethan-1-ol had the following physicochemical properties.

1. temperaturewhile the reaction mixture was refluxed at80° C
2. concentrationThe reaction mixture was once concentrated under a reduced pressure, and extraction
3. customdried
4. additionby adding magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated under a reduced pressure
7. customThe residual substance was purified by chromatography
8. customthe solvent of the fraction obtained from ether
9. distillationethyl acetate=1:1 eluent was distilled
10. customa colorless oily substance was obtained

ORD record

ord-bc893b1a5c624f08b82bbc2e7672aafd

Source dataset

uspto-grants-1994_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05374653