SU357194A1 - METHOD OF OBTAINING 1,3,5,7-TETRABROMADAMANTANDIOL-2,6 - Google Patents
METHOD OF OBTAINING 1,3,5,7-TETRABROMADAMANTANDIOL-2,6Info
- Publication number
- SU357194A1 SU357194A1 SU1479037A SU1479037A SU357194A1 SU 357194 A1 SU357194 A1 SU 357194A1 SU 1479037 A SU1479037 A SU 1479037A SU 1479037 A SU1479037 A SU 1479037A SU 357194 A1 SU357194 A1 SU 357194A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- obtaining
- tetrabromadamantandiol
- sodium borohydride
- tetrabromadamantaidiol
- mol
- Prior art date
Links
- 238000000034 method Methods 0.000 description 4
- YOQDYZUWIQVZSF-UHFFFAOYSA-N sodium borohydride Chemical group [BH4-].[Na+] YOQDYZUWIQVZSF-UHFFFAOYSA-N 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- ODGROJYWQXFQOZ-UHFFFAOYSA-N sodium;boron(1-) Chemical group [B-].[Na+] ODGROJYWQXFQOZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Chemical class C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 235000015450 Tilia cordata Nutrition 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229940052761 dopaminergic Adamantane derivatives Drugs 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N n-heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000005020 pharmaceutical industry Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Description
Изобретение относитс к способу получени повых адамантановых производных, в частности к способу получени 1,3,5,7-тетрабромадамантандиола-2 ,6, которые могут найти применение в фармацевтической промышленности , а также в промышленности тонкого органического синтеза.This invention relates to a process for the preparation of new adamantane derivatives, in particular, to a process for the preparation of 1,3,5,7-tetrabromoadmantane-2, 6, which can be used in the pharmaceutical industry, as well as in the fine organic synthesis industry.
Известно восстановление кетогруппы различных углеводородов, замещенных бромом, боргидридом натри в среде различных органических растворителей.It is known to reduce the keto group of various hydrocarbons substituted by bromine, sodium borohydride in the environment of various organic solvents.
По предлагаемому способу получают 1,3,5,7тетрабромадамантандиол-2 ,6. Процесс восстановлени боргидритом натри ведут в водно-спиртовой среде При О-50°С в течение 0,5-2 час.According to the proposed method receive 1,3,5,7 tetrabromaine dandiol-2, 6. The process of sodium borohydrite reduction is carried out in an aqueous-alcoholic medium. At O-50 ° C for 0.5-2 hours.
Пример. В стекл нном реакторе смешивают 1 г 1,3,5,7-тетрабромадамантаидиола-2,6 (0,002 моль) в 12 мл метанола с раствором 0,4 г (0,01 моль) боргидрида натри тз 13 мл воды. Температуру реакции 20-25°С поддерживают с помошью холодной бани и выдерживают 1 час. Осадок отфильтровывают, промывают водой и подсушивают.Example. In a glass reactor, 1 g of 1,3,5,7-tetrabromadamantaidiol-2,6 (0.002 mol) is mixed in 12 ml of methanol with a solution of 0.4 g (0.01 mol) of sodium borohydride TK 13 ml of water. The reaction temperature of 20-25 ° C is maintained with the aid of a cold bath and kept for 1 hour. The precipitate is filtered off, washed with water and dried.
Продукт очищают перекристаллизацией из гептана Тпл. 205-207°С. Выход 50%.The product is purified by recrystallization from heptane Tpl. 205-207 ° C. Yield 50%.
ИК-спектр не содержит полосы в области 1730-1740 ел;-. Иптенсивные полосы по вл ютс в област х 1100 и 3500 см, характерные дл гидроксильной группы.The IR spectrum does not contain bands in the 1730-1740 area; -. Intensive bands appear in the 1100 and 3500 cm regions characteristic of the hydroxyl group.
Найдено, %: С 25,0;Н 2,43; Вг 62,79.Found,%: C 25.0; H 2.43; Br 62.79.
CioHi2O2Br4.CioHi2O2Br4.
Вычислено, %: С 24,6; П 2,46; Вг 66,12. Предмет изобретени Calculated,%: C 24.6; P 2.46; Br 66.12. Subject invention
Способ получени 1,3,5,7-тетрабромадамантаидиола-2 ,6, отличающийс тем, что, 1,3,5,7-тетрабро.мадамаитандиол-2,6 подвергают восстановлению боргидридом натри в водно-спиртовой среде при О-50°С с последующим выделением продукта известиымп приемами.The method of obtaining 1,3,5,7-tetrabromadamantaidiol-2, 6, characterized in that 1,3,5,7-tetrabromamamamitandiol-2,6 is subjected to reduction with sodium borohydride in an aqueous-alcoholic medium at -50 ° With the subsequent release of the product by means of lime techniques.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU357194A1 true SU357194A1 (en) |
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