[phenyl-(2,2,2-trifluoroacetyl)oxy-lambda3-iodanyl] 2,2,2-trifluoroacetate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 1-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]piperidine-4-carboxamide (528 mg) in a mixed solvent of ethanol (10 mL) and acetonitrile (10 mL) was added [bis(trifluoroacetoxy)iodo]benzene (884 mg). The mixture was stirred at room temperature overnight and evaporated. Saturated aqueous sodium hydrogen carbonate was added to the residue and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was applied to a column of silica gel and purified using chloroform-methanol (20:1) as an eluent to give the title compound. evaporated Saturated aqueous sodium hydrogen carbonate was added to the residue extracted with chloroform The organic layer was washed with brine dried over anhydrous magnesium sulfate evaporated purified

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (4.3 g, 17.7 mmol), [bis(trifluoroacetoxy)iodo]benzene (15.6 g, 36.2 mmol), H2O (18 ml), CF3CO2H (2.8 ml) and CH3CN (90 ml) was refluxed for 3 hours. The CH3CN was removed under reduced pressure and the resulting yellow liquid was partitioned between H2O and CH2Cl2. The biphasic mixture was filtered, the organic phase collected, washed with saturated NaHCO3 solution and concentrated to afford 1.5 g of an amorphous brown solid. The solid was flash chromatographed on silica gel, eluting the column with 5% EtOAc/CH2Cl2. Concentration of similar fractions afforded 0.7 g of the compound as a pale yellow solid, m.p. 99°-101° C. The CH3CN was removed under reduced pressure the resulting yellow liquid was partitioned between H2O and CH2Cl2 The biphasic mixture was filtered the organic phase collected washed with saturated NaHCO3 solution concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (4.3 g, 17.7 mmol), [bis(trifluoroacetoxy)iodo]benzene (15.6 g, 36.2 mmol), H2O (18 ml), CF3CO2H (2.8 ml) and CH3CN (90 ml) was refluxed for 3 hours. The CH3CN was removed under reduced pressure and the resulting yellow liquid was partitioned between H2O and CH2 Cl2. The biphasic mixture was filtered, the organic phase collected, washed with saturated NaHCO3 solution and concentrated to afford 1.5 g of an amorphous brown solid. The solid was flash chromatographed on silica gel, eluting the column with 5% EtOAc/CH2Cl2. Concentration of similar fractions afforded 0.7 g of the compound as a pale yellow solid, m.p. 99°-101° C. The CH3CN was removed under reduced pressure the resulting yellow liquid was partitioned between H2O and CH2 Cl2 The biphasic mixture was filtered the organic phase collected washed with saturated NaHCO3 solution concentrated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To (S)-Benzyl 3-carbamoyl-3-methylpyrrolidine-1-carboxylate (35.61 g, 135.8 mmol) in 1:1 MeCN/H2O (100 mL) was added [bis(trifluoroacetoxy)iodo]benzene (58.38 g, 135.8 mmol). The reaction mixture was stirred at ambient temperature for 2 hours and then at 86° C. (bath) for 2 hours. After cooling to ambient temperature, concentrated HCl (14.85 g, 407.3 mmol) and ether (200 mL) were added. The aqueous layer was separated and basified by K2CO3 (46.91 g, 339.4 mmol). To the resulting solution was added THF (150 mL) and Boc2O (37.04 g, 169.7 mmol). The reaction mixture was stirred at ambient temperature for 1 hour. Ethyl acetate (100 mL) was added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (3:1 hexane/ethyl acetate) on silica gel to give (S)-benzyl 3-(tert-butoxycarbonylamino)-3-methylpyrrolidine-1-carboxylate (42.30 g, 126.5 mmol, 93.2% yield) as an oil. at 86° C. (bath) for 2 hours After cooling to ambient temperature The aqueous layer was separated The reaction mixture was stirred at ambient temperature for 1 hour The organic layer was separated washed with brine dried (sodium sulfate) filtered concentrated under reduced pressure The residue was purified by flash chromatography (3:1 hexane/ethyl acetate) on silica gel