2-(2,6-dimethylmorpholin-4-yl)ethanol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a flask was added 5.0 g. (0.03 mole) of 4-(2-hydroxyethyl)-2,6-dimethylmorpholine in 50 ml. of carbon tetrachloride followed by 10.2 g. (0.04 mole) of triphenylphosphine. The mixture was stirred at reflux for three hours, then the reaction was cooled to 0° C., the triphenylphosphine oxide was filtered and the solvent stripped. The residue was dissolved in 10% aqueous hydrochloric acid and the by-products were extracted into ethyl acetate. The acid layer was then basified with ammonium hydroxide and extracted into ethyl acetate. The ethyl acetate solution was dried with magnesium sulfate, filtered, and concentrated. The crude product was further purified by flash chromatography to give 2.31 g. (43% yield) of 4-(2-chloroethyl)-2,6-dimethylmorpholine as a colorless liquid. To a flask was added 5.0 g at reflux for three hours the triphenylphosphine oxide was filtered The residue was dissolved in 10% aqueous hydrochloric acid the by-products were extracted into ethyl acetate extracted into ethyl acetate The ethyl acetate solution was dried with magnesium sulfate filtered concentrated The crude product was further purified by flash chromatography to give 2.31 g

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a flask was added 22.8 g. (0.6 mole) of lithium aluminum hydride in 300 ml. of dimethyl ether. The stirred slurry was cooled to 0° C. and then 26.5 g. (0.15 mole) of ethyl 2,6-dimethyl-4-morpholinylacetate was slowly added. The reaction was allowed to warm to room temperature and stirred for 18 hours. It was then quenched with aqueous ammonium chloride, filtered, and extracted with diethyl ether. The solvent was concentrated to give 15.5 g. (67% yield) of the desired intermediate. To a flask was added 22.8 g to warm to room temperature It was then quenched with aqueous ammonium chloride filtered extracted with diethyl ether The solvent was concentrated to give 15.5 g

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a flask was added 22.8 g. (0.6 mole) of lithium aluminum hydride in 300 ml. of dimethyl ether. The stirred slurry was cooled to 0° C. and then 26.5 g. (0.15 mole) of ethyl 2,6-dimethyl-4-morpholinylacetate was slowly added. The reaction was allowed to warm to room temperature and stirred for 18 hours. It was then quenched with aqueous ammonium chloride, filtered, and extracted with diethyl ether. The solvent was concentrated to give 15.5 g. (67% yield) of the desired intermediate. To a flask was added 22.8 g to warm to room temperature It was then quenched with aqueous ammonium chloride filtered extracted with diethyl ether The solvent was concentrated to give 15.5 g

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a flask was added 22.8 g. (0.6 mole) of lithium aluminum hydride in 300 ml. of dimethyl ether. The stirred slurry was cooled to 0° C. and then 26.5 g. (0.15 mole) of ethyl 2,6-dimethyl-4-morpholinylacetate was slowly added. The reaction was allowed to warm to room temperature and stirred for 18 hours. It was then quenched with aqueous ammonium chloride, filtered, and extracted with diethyl ether. The solvent was concentrated to give 15.5 g. (67% yield) of the desired intermediate. To a flask was added 22.8 g to warm to room temperature It was then quenched with aqueous ammonium chloride filtered extracted with diethyl ether The solvent was concentrated to give 15.5 g