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Preparation 12 To a solution of dl-1,2-diaminopropane (1.48 g, 20.0 mmol) and sodium carbonate (2.73 g, 22.0 mmol) in dioxane (100.0 mL) and water (100.0 mL) was added di-tert-dicarbonate (4.80 g, 22.0 mmol) at room temperature. The resulted mixture was stirred for 14 hr. Dioxane was removed in vacuo. The precipitate was filtered off and the filtrate was concentrated in vacuo to dryness. The residue was triturated with EtOAc and then filtered. The filtrate was concentrated in vacuo to dryness to give a mixture of dl-1-amino-2-(1,1-dimethylethoxy)carbonylamino-propane and dl-2-amino-1-(1,1-dimethylethoxy)carbonylamino-propane which were not separable by normal chromatography method. The mixture was used for the reaction in Example 8.
2
[ 6627-89-0 ]
[ 78-90-0 ]
[ 149632-73-5 ]
[ 255735-88-7 ]
Yield
Reaction Conditions
Operation in experiment
In ethanol; for 16h;Reflux;
(+/-)- ,2-diaminopropane (2.30 mL, 27.0 mmol) was dissolved in ethanol (100 mL) and 1 ,1-dimethy.ethyl phenyl carbonate (9.98 mL, 54.0 mmol) added. The mixture was heated to reflux for 16 hours, cooled to room temperature, and concentrated by rotovap. The residue was diluted with water before hydrochloric acid (1 M) was added carefully until the pH was ~3. The aqueous phase was washed 3 times withdichloromethane and then made strongly basic with sodium hydroxide (1 M). The aqueous phase and extracted 3 times with dichloromethane and the combined organic layers dried over sodium sulfate before being concentrated to give the title compound (2.98 g, 63percent) as a mixture (-85:15) of regioisomers. ES-LCMS m/z: 175 (M+1 ).
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