反应详情

(1RS, 2SR, 3RS)-3-[2-(3-Hydroxyprop-1-yloxy)-4-methoxyphenyl]-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylic acid (0.07 g, 0.13 mmol) was dissolved in dry dichloromethane (0.5 ml) and Dess-Martin periodinane (0.07 g, 0.17 mmol) added in dry dichloromethane (1 ml). After 2h. the product was partitioned between ether and saturated aqueous sodium carbonate solution containing sodium thiosulfate. The ether extract was washed with water then brine, dried (MgSO4 anhydrous), filtered and evaporated to give an oil which was used without purification. The crude product was dissolved in t-butanol (5 ml) and to this was added a solution of sodium chlorite (1 8 mg, 0.2 mmol) and sulfamic acid (21 mg, 0.22 mmol) in water (1.5 ml). After 1 h. stirring at ambient temperature the product was extracted into ethyl acetate. The organic layer was washed with water then brine then dried (MgSO4 anhyd.) filtered and evaporated to give an oil. The product was purified by column chromatography on silica-gel (eluant: ethyl acetate/hexane/3% acetic acid) to give 12 mg of free acid which was converted to its bis-dicyclohexylamine salt.

1. customAfter 2h. the product was partitioned between ether and saturated aqueous sodium carbonate solution
2. additioncontaining sodium thiosulfate
3. extractionThe ether extract
4. washwas washed with water
5. dry with materialbrine, dried (MgSO4 anhydrous)
6. filtrationfiltered
7. customevaporated
8. customto give an oil which
9. customwas used without purification
10. dissolutionThe crude product was dissolved in t-butanol (5 ml)
11. extractionwas extracted into ethyl acetate
12. washThe organic layer was washed with water
13. dry with materialbrine then dried (MgSO4 anhyd.)
14. filtrationfiltered
15. customevaporated
16. customto give an oil
17. customThe product was purified by column chromatography on silica-gel (eluant: ethyl acetate/hexane/3% acetic acid)