Hydrochloric Acid → HCID 67421473, compound

Participants

Reaction Steps

To a solution of the triketo ester 8 (0.1 g, 0.22 mmol) in CH2Cl2 (8 ml) tert-butylamine-borane complex (0.1 g, 1.12 mmol) was added and the reaction was refluxed overnight. The reaction was cooled to room temperature 3N HCl was added and the resulting mixture was stirred for 30 min. The organic layer was separated, washed with a saturated aqueous solution of sodium bicarbonate (10 ml), water (10 ml), was dried over anhydrous sodium sulfate and evaporated to dryness. The residue, in which the 7-ketone was not reduced, was dissolved in a mixture 1:4 v/v of H2O/THF (5 ml) and NaBH4 was added at 0° C. The mixture was stirred at room temperature for 30 min, then water (5 ml) and 3N HCl (5 ml) were added. The mixture was extracted with EtOAc (4×30 ml), the combined organic layers were dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure. The residue, which consist of at least 2 components, was purified by flash chromatography, using from 1 to 4% MeOH in CHCl3 to yield 0.036 g (0.08 mmol, 36%) of the desired compound 9.

Provenance & Evidence