The chemical industry reduces the impact on the environment during synthesis Diethyl 2-bromo-2-methylmalonate. I believe this compound will play a more active role in future production and life.
Synthetic Route of 29263-94-3, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 29263-94-3, name is Diethyl 2-bromo-2-methylmalonate, This compound has unique chemical properties. The synthetic route is as follows.
To a solution of the compound of Reference Example 61 (176 g) in tetrahydrofuran (1000 ml) were addded tetrakistriphenylphosphine palladium (2.21 g) and morpholine (200 g), and the mixture was stirred at room temperature. Twenty-five minutes later, to the reaction solution were added a 5 % aqueous potassium hydrogen sulfate solution and ethyl acetate, and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure to give 2-methyl-2-propanyl (3R)-3-{[(4-hydroxy-2-methyl-5-nitrophenyl)carbonyl](2-propanyl)amino}-1-piperidinecarboxylate (156 g). To a solution of the obtained 2-methyl-2-propanyl (3R)-3-{[(4-hydroxy-2-methyl-5-nitrophenyl)carbonyl](2-propanyl)amino}-1-piperidinecarboxylate (138 g) in N,N-dimethylformamide (1000 ml) were added potassium carbonate (91 g), diethyl 2-bromo-2-methylmalonate (94 g), and the mixture was stirred at 80C for 8 hours. The reaction solution was allowed to cool to room temperature, filtered through celite, and to the filtrate were added a 5 % aqueous sodium hydrogen sulfate solution and ethyl acetate, and extracted with ethyl acetate. The organic layer was washed with water, a saturated aqueous sodium chloride solution, and then dried over sodium sulfate. The sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure to give diethyl methyl(5-methyl-4-{[(3R)-1-{[(2-methyl-2-propanyl)oxy]carbonyl}-3-piperidinyl](2-propanyl)carbamoyl}-2-nitrophenoxy)propanedioate (205 g). Subsequently, to a suspension of iron (110 g) in acetic acid (500 ml) was added dropwise a solution of the obtained diethyl methyl(5-methyl-4-{[(3R)-1-{[(2-methyl-2-propanyl)oxy]carbonyl}-3-piperidinyl](2-propanyl)carbamoyl}-2-nitrophenoxy)propanedioate (205 g) in acetic acid (200 ml) slowly at 90C. Ten hours later, the mixture was allowed to cool to room temperature, filtered through celite, and the filtrate was concentrated under reduced pressure. To the obtained residue was added a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with chloroform. The organic layer was washed with water and a saturated aqueous sodium chloride solution, dried over sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel chromatography to give the title compound (102 g). Rf = 0.25 (n-hexane/ethyl acetate=1/1)
The chemical industry reduces the impact on the environment during synthesis Diethyl 2-bromo-2-methylmalonate. I believe this compound will play a more active role in future production and life.
Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP2447264; (2012); A1;,
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