Реакция #588576

Уравнение реакции

sodium borohydride

ethanol

sodium borohydride

hydrochloric acid

t-butyl 4-[1-(2-butynyl)-5-ethoxycarbonyl-4-methylsulfanyl carbonyl-1H-imidazol-2-yl]piperazine-1-carboxylate

→

title compound

Выход 25.5%

t-Butyl 4-[1-(2-butynyl)-5-ethoxycarbonyl-4-hydroxymethyl-1H-imidazol-2-yl]piperazine-1-carboxylate

Выход 25.5%

Растворители

ethyl acetate

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 15 hours
2. 2
   Промывкаthe organic layer was washed successively with 50 ml of water and 50 ml of a saturated sodium chloride solution
3. 3
   СушкаThe mixture was dried over anhydrous magnesium sulfate
4. 4
   Концентрированиеconcentrated under reduced pressure
5. 5
   ДругоеThe residue was purified by silica gel column chromatography
6. 6
   Другое0.172 g of the starting material was collected from the fraction
7. 7
   Промывкаeluted with hexane-ethyl acetate (4:1)

Методика

0.187 g of mercury (II) acetate and 0.090 of sodium borohydride were added to 8 ml of an ethanol solution containing 0.265 g of t-butyl 4-[1-(2-butynyl)-5-ethoxycarbonyl-4-methylsulfanyl carbonyl-1H-imidazol-2-yl]piperazine-1-carboxylate at 0° C., and the mixture was stirred at room temperature for 4 hours. After 0.187 g of mercury (II) acetate and 0.090 of sodium borohydride had been added to the solution, the mixture was stirred at room temperature for 15 hours. 100 ml of ethyl acetate and 50 ml of 0.5N hydrochloric acid were added to the solution, and the organic layer was washed successively with 50 ml of water and 50 ml of a saturated sodium chloride solution. The mixture was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography. 0.172 g of the starting material was collected from the fraction eluted with hexane-ethyl acetate (4:1). Then, 0.061 g of the title compound was obtained from the fraction eluted with hexane-ethyl acetate (1:4).

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