The synthesis process Mibolerone its structural characterization
|School||Central South University|
|Keywords||The Mibo Long (Mibolerone) Steroidal Synthesis Mass Spectrometry NMR spectra|
Mibo a dragon (Mibolerone) of the assimilation of a high pharmacodynamics low side effects of hormone drugs, physical constants, spectroscopic properties, specific synthetic method has not been reported in the literature. This article studies the the the dehydro compound synthetic process by Mibo the Dragon (Mibolerone) and its intermediate methyl nandrolone, as well as methyl nandrolone 6. The structure of the intermediates and target compounds by infrared spectroscopy (IR), carbon-13 nuclear magnetic resonance spectrum ( 13 sup> CNMR), hydrogen Nuclear Magnetic Resonance Spectrum ( 1 sup> HNMR), mass spectrometry (MS ), modern physical methods to characterize and mass spectral fragmentation mechanism was discussed. The two synthetic route design on the basis of the literature. The first is an alkaline decarboxylation product (chemical name for estr-5 (10) - ene-3 ,17 - dione), as raw material, methanol selective protection of the 3-carbonyl group, and then with methyl lithium 17-carbonyl group introduction of methylation reaction of 17 - methyl-, methyl nandrolone, dehydrogenation reaction occurs then tetrachlorobenzoquinone with methyl nandrolone the introduction of six double bonds, and then with dimethyl copper lithium methyl nandrolone 6 dehydro compound Michael addition reaction to obtain the objective compound. The preparation of the second line on the methyl nandrolone, the target compounds with the first route. The difference is methyl nandrolone 6 dehydro compound was prepared, this method based on the nitrogen-bromosuccinimide (NBS) bromine, and then off the introduction of hydrogen bromide methyl nandrolone 6 double bonds . Methyl nandrolone synthesis process. Traditional crafts in acidic decarboxylation as raw material, the three carbonyl to the triethyl orthoformate selective protection, this step-by-step yield of only 42%. In the new process, methanol selective protection alkaline decarboxylation of the 3-carbonyl group, and the yield up to 100%. Methanol inexpensive and easy to get, mild reaction conditions, easy to operate. Methyl nandrolone preparation process were studied the influence of the synthetic yield as a reaction system with anhydrous diethyl ether, tetrahydrofuran, benzene and anhydrous ethyl ether mixed solvent, the yield was 32%, 41.3%, 37%, determine the preferred solvent system of tetrahydrofuran. At the same time instead of methyl iodide, methyl lithium reagent 17 carbonyl reaction, the yield increased to 51% from 37%. 6 dehydro compound synthesis process were studied. Methyl nandrolone 6 dehydrogenation reaction is based on the tetrachlorobenzoquinone directly off seven hydrogen atoms into the double bond, and the yield up to 64%. Were studied in the hydrochloric acid catalyzed tert-butanol, ethyl acetate, tetrahydrofuran, as a solvent system, its yield was 24%, 56%, 64%. Meanwhile, to the NBS method of introduction of a methyl nandrolone 6 double bonds, found in experiments that the 3-carbonyl group is selectively protected reaction yield is low, only 42% bromide, by thin layer chromatography plate (TLC) observed byproducts, post-processing difficulties. The target compound synthesis process of Mibo dragon. Dry tetrahydrofuran as solvent, and the two field-based copper file with 6 dehydro compound Michael (Michael) 1,6 total conjugate addition reaction directly obtained target molecule to Mibo Long, the yield was 50%. This synthetic route total yield of 16.3%, and to optimize the reaction conditions, shortening the synthesis process, for further in-depth study of the final expected as the commercialization of the process route.