Hydrochloric Acid → HCID 67421473, compound

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.

1. temperaturethe reaction was refluxed overnight
2. additionwas added
3. customThe organic layer was separated
4. washwashed with a saturated aqueous solution of sodium bicarbonate (10 ml), water (10 ml)
5. dry with materialwas dried over anhydrous sodium sulfate
6. customevaporated to dryness
7. dissolutionwas dissolved in a mixture 1:4 v/v of H2O/THF (5 ml) and NaBH4
8. additionwas added at 0° C
9. stirringThe mixture was stirred at room temperature for 30 min
10. additionwater (5 ml) and 3N HCl (5 ml) were added
11. extractionThe mixture was extracted with EtOAc (4×30 ml)
12. dry with materialthe combined organic layers were dried over anhydrous sodium sulphate
13. customevaporated to dryness under reduced pressure
14. customwas purified by flash chromatography

ORD record

ord-d3e6a34e38114470a286c64adcc9acca

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08999964B2