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A synthetic method, cholesterol technology, applied in the direction of steroids, organic chemistry, etc., can solve the problems of large consumption of raw and auxiliary materials, long steps, uneconomical, etc., and achieve the effect of less raw and auxiliary materials, low cost and high yield
Inactive Publication Date: 2015-10-07
HUNAN KEREY BIOTECH
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[0006] The existing method uses turmeric extract saponin as raw material to obtain cholesterol (01) through 6-step reaction. The steps are long, the yield is low, the consumption of raw and auxiliary materials is large, the pollution is large, and it is uneconomical.
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Embodiment 1
[0032] The present embodiment is the synthetic method of cholesterol, specifically comprises the following steps:
[0033] (1) Synthesis of compound 03
[0034] (a) In a 2000ml glass reaction bottle, add 1200ml of toluene, stir, add 63g of triphenylphosphine, heat to reflux, steam and divide water until the toluene is clear, stop heating, cool down to below 40°C under nitrogen protection, add 1-chloro - 29 g of 4-methylpentane, heated under reflux for 2 hours to obtain 4-methylpentyltriphenylphosphine chloride solution;
[0035] (b) The 4-methylpentyltriphenylphosphine chloride solution is cooled under nitrogen protection to below 20°C, and 32 g of potassium tert-butoxide is added in stages to obtain the witting reagent, and after stirring for 30 minutes, the witting reagent is added Pregnenolone 50g, after adding, heat and reflux reaction for 4 hours, after the plate reaction is complete;
[0036] (c) ice-water bath is cooled to below 10 ℃, slowly changes in the acid soluti...
Embodiment 2
[0040] The difference between this embodiment and Example 1 is that in this embodiment, triphenylphosphine, 1-chloro-4-methylpentane, potassium tert-butoxide, 30% industrial concentrated The amount of hydrochloric acid was adjusted to 94g, 44g, 48g and 58g respectively to finally obtain compound 0354.66g with a molar yield of 89.96%.
Embodiment 3
[0042] The difference between this example and Example 1 is that in this example, the amount of triphenylphosphine, 1-chloro-4-methylpentane, and potassium tert-butoxide in step (1) is adjusted to 125g respectively , 58g, 48g and 64g, 30% industrial concentrated hydrochloric acid was replaced by 32g concentrated sulfuric acid, finally compound 0354.88g was obtained, and the molar yield was 90.32%.
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Abstract
The invention relates to a synthetic method of cholesterol. The synthetic method of the cholesterol specifically comprises the following steps that 1, firstly, triphenylphosphine and 1-chlorine-4-methylpentane are used to react to obtain a 4-methyl pentyl triphenyl phosphonium chloride solution, then potassium tert-butoxide or sodium tert-butoxide is added to react to obtain a witting reagent, a witting reaction occurs by adding pregnenolone into the witting regent, and a compound 03 is obtained through extracting after complete reaction; 2, under the action of chirality phosphine ligand and a rhodium catalyst, an asymmetric hydrogenation reaction occurs to the compound to obtain the cholesterol. According to the synthetic method of the cholesterol, a 6-step reaction of an existing method is simplified into a 2-step reaction, and meanwhile the ring-opening reaction consuming a large amount of hydrochloric acid and zinc powder is omitted. The technology is simple, the consumption of raw materials is less, the yield is high, the cost is low, environmental protection is achieved, so that the economical effect and the environmental protection are achieved, and the industrial implementation is facilitated.
Description
technical field [0001] The present invention relates to the synthesis of a steroid compound, in particular to a method for synthesizing cholesterol. Background technique [0002] Cholesterol, also known as cholesterol, is a derivative of cyclopentane polyhydrophenanthrene. As early as the 18th century, people had discovered cholesterol from gallstones. In 1816, chemists named this lipid-like substance cholesterol. Cholesterol is widely present in animals, especially in brain and nerve tissue, and is also high in kidney, spleen, skin, liver and bile. Cholesterol is an indispensable and important substance in animal tissue cells. It not only participates in the formation of cell membranes, but also is a raw material for the synthesis of bile acids, vitamin D and steroid hormones. [0003] At present, cholesterol is mainly extracted from the brains and spines of pigs, cattle, sheep and other animals. Due to the emergence of mad cow disease and Streptococcus suis infection, pe...
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