2-phenoxyacetonitrile

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 20 millimoles (2.66 g) of phenoxyacetonitrile in 6 ml of anhydrous ether, is added a solution of 30 millimoles (1.5 eg) of benzylmagnesium bromide in 6 ml of anhydrous ether. The mixture sets to a mass and 10 ml of tetrahydrofuran are added. After stirring for 2 hours at room temperature, the reaction mixture is cooled by an ice-bath, then added with 50 ml of a normal solution of sodium cyanide in dimethylformamide. After 2 hours of stirring at room temperature, the mixture is hydrolyzed by 10 ml of methanol then by pasty sodium sulfate. There are obtained 3.45 g of raw product, which purified by high pressure liquid chromatography on silica, with a solution by ethyl acetate/petroleum ether 1/1, give 0.3 g of 2-amino-2-benzyl-3-phenoxy-propionitrile. Yield: 6.3% are added the reaction mixture is cooled by an ice-bath After 2 hours of stirring at room temperature There are obtained 3.45 g of raw product, which purified by high pressure liquid chromatography on silica, with a solution by ethyl acetate/petroleum ether 1/1

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 10 millimoles (1.33 g) of phenoxyacetonitrile are dissolved in 10 ml of anhydrous toluene at 0° C., under an argon atmosphere. A solution of vitridenide (NaH2AL1 [0-CH2 -CH2OCH3 ]2) at 70% in toluene (1,4 ml viz 0.5 eq) in 3 m of anhydrous toluene is added, dropwise, at this temperature. The stirring is maintained for 1 hour at 0° C., then 2 ml (1.5 eq) of trimethylsilyl cyanide are added. The reaction mixture is maintained at room temperature for 3 hours, while stirring, then hydrolyzed by usual way. After purification by acid base extraction, there are obtained 0.300 g of 2-amino-3-phenoxy propionitrile with a yield of 20%. The reaction mixture is maintained at room temperature for 3 hours After purification by acid base extraction, there

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 5 millimoles (0.665 g) of phenoxy-acetonitrile are dissolved in 8 ml of anhydrous toluene at 0° C., under an argon atmosphere 7.5 millimoles of a toluenic solution 1.5M of diisobutylaluminum hydride (5 ml) are added dropwise, at this temperature. The stirring is maintained for 1 hour at 0° C., then 5.9 ml (1.3 eq) of diethylaluminum cyanide are added. The reaction mixture is stirred for 3 hours at room temperature, then hydrolyzed with 4 ml of methanol and pasty sodium sulfate. After purification by high pressure liquid chromatography on silica, there are obtained 0.182 g of 2-amino-3-phenoxy-propionitrile, in form of a cream-colored solid- state product; M.P. 65° C., yield: 22%. are added dropwise, at this temperature After purification by high pressure liquid chromatography on silica, there

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 5 millimoles (0.665 g) of phenoxy-acetonitrile are dissolved in 8 ml of anhydrous toluene at 0° C., under an argon atmosphere 7.5 millimoles of a toluenic solution 1.5M of diisobutylaluminum hydride (5 ml) are added dropwise, at this temperature. The stirring is maintained for 1 hour at 0° C., then 5.9 ml (1.3 eq) of diethylaluminum cyanide are added. The reaction mixture is stirred for 3 hours at room temperature, then hydrolyzed with 4 ml of methanol and pasty sodium sulfate. After purification by high pressure liquid chromatography on silica, there are obtained 0.182 g of 2-amino-3-phenoxy-propionitrile, in form of a cream-colored solid- state product; M.P. 65° C., yield: 22%. are added dropwise, at this temperature After purification by high pressure liquid chromatography on silica, there

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

実験手順: To a stirring solution of the 2-[8-(benzyloxy)quinolin-7-yl]-1-phenylethanol (0.302 mmol) in phenoxyacetonitrile (9.05 mmol, 30 eq.) at −10° C. was dropwise added conc. sulfuric acid (1.51 mmol, 5.0 eq.). On completion of addition, the reaction mixture was allowed to warm to room temperature and was stirred 16 h. The reaction was then diluted with ice that was allowed to melt and was then stirred 2 h. The mixture was next brought to pH=7 by the addition of saturated aqueous sodium bicarbonate solution and then diluted with water (5 mL) and extracted with ethyl acetate (2×5 mL). The organic layers were combined, dried (MgSO4), filtered and concentrated to give sulfuric acid mono-{7-[2-(2-phenoxy-acetylamino)-2-phenyl-ethyl]-quinolin-8-yl}ester as a yellow oil that was purified by column chromatography using 20% methanol/dichloromethane. To a stirring suspension of the sulfuric acid mono-{7-[2-(2-phenoxy-acetylamino)-2-phenyl-ethyl]-quinolin-8-yl}ester (0.089 mmol, 1.0 eq.) from the initial step in methanol (9 mL) was added 3N HCl (18 mL) and the resulting suspension was heated to 55° C. and stirred 2 h. The reaction mixture was then cooled to room temperature and organic solvents were removed by rotary evaporation resulting in a precipitate that was filtered yielding the pure product as a yellow solid (0.059 mmol, 12% for 2 steps). HRMS: calcd for C25H22N2O3+H+, 399.17032; found (ESI-FTMS, [M+H]1+), 399.17059. at −10° C. On completion of addition The reaction was then diluted with ice that was then stirred 2 h extracted with ethyl acetate (2×5 mL) dried (MgSO4) filtered concentrated