HCID 13826515, compound → HCID 13826517, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 0.710 g. (0.0187 mole) of lithium aluminum hydride, 80 ml. of tetrahydrofuran and 4.85 g. (0.0057 mole) of [1α,3β,24R]-1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-25-(1-ethoxyethoxy)-24-fluorocholest-5-en-21-ol 21-(4-methylbenzenesulfonate) was heated at reflux (60° C.) for 1 hr and cooled to 0° C. The mixture was diluted with 200 ml. of ether and quenched with the dropwise addition of 1.4 ml. of water and 1.1 ml. of 10% aqueous sodium hydroxide solution. The mixture was then stirred for 1 hr and filtered. The solids were triturated with ether and filtered. The combined filtrates were evaporated to dryness and chromatographed on 0.06-0.20 mm silica gel to yield [1α,3β,24R]-1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-25-(1-ethoxyethoxy)-24-fluorocholest-5-ene, [α]D20 +7° (c 1, CHCl3 ).

Provenance & Evidence