Tetrahydrofuran → HCID 87571648, compound

Participants

Reaction Steps

To a stirred solution of (E)-3-(2-aminoethoxyimino)-4,4-dimethylandrostane-5α,6α,17β-triol (Example 16, 109 mg) in dioxane (3.5 ml) and water (0.4 ml), NBS (112 mg) was added. After 5 h THF (15 ml) and brine (20 ml) were added and the mixture stirred for 10 min. The phases were separated and the aqueous phase was extracted with THF. The combined organic extracts were washed with aqueous NaHSO3, brine, dried over MgSO4, filtered and evaporated to dryness. The crude product was purified by flash chromatography (SiO2, DCM/MeOH/26% NH4OH 90/10/1). To the concentrated fractions a stoichiometric amount of fumaric acid in MeOH was added and evaporated to dryness. The residue was triturated with Et2O for 0.5 h and the precipitate was filtered to give the title compound as a white solid (58 mg, 55%).

Provenance & Evidence