Method for synthesizing pregnenolol acetate and congener thereof

A kind of technology of pregnenone alcohol acetate and synthetic method, which is applied in the direction of steroidal compounds and organic chemistry, can solve the problems of unfavorable mass production of pregnenone alcohol acetate, environmental pollution, and low three-step total yield, and achieve mild conditions , Simple equipment and easy operation

Inactive Publication Date: 2011-08-17
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Except that the total yield of the three steps is not high (less than 60%) in this patented method, pyridine hydrochloride, which pollutes the environment, is required for the cracking of steroidal saponin, and special light such as a medium-pressure mercury lamp is required for the photochemical reaction. Reactor and highly toxic solvent acetonitrile, benzene, etc. These conditions are not conducive to mass production of pregnenone alcohol acetate in the future
[0006] The problem to be solved is to realize a method with mild conditions, easy operation, high yield and low pollution to synthesize pregnenone acetate, so as to solve the environmental pollution problem in the production process of steroidal sapogenin degradation reaction

Method used

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  • Method for synthesizing pregnenolol acetate and congener thereof
  • Method for synthesizing pregnenolol acetate and congener thereof
  • Method for synthesizing pregnenolol acetate and congener thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Synthesis of Example 1 Compound 1a

[0019]

[0020] 100 g of compound 2a, 150 ml of acetic anhydride and 52 ml of acetic acid were reacted at a pressure of 0.6 MPa and a temperature of 200° C. for 1 hour. Transfer the reaction solution to a distillation flask, recover the unreacted acetic anhydride and acetic acid under reduced pressure, dissolve the residue with 21 cyclohexane, then add 0.7 g of tetraphenylporphyrin, react with incandescent lamp for 3 hours and complete the reaction of all raw materials , add 1.31ml of concentrated sulfuric acid, heat to reflux and stir for 14 hours and then the reaction is complete. After cooling, wash with water and saturated aqueous sodium carbonate solution, then with saturated saline, dry over anhydrous sodium sulfate, evaporate the solvent under reduced pressure, and recrystallize from ethanol to obtain compound 1a 64.5 g, the yield is 75%.

[0021] 1 H-NMR (400MHz, CDCl 3 ( d, 2H, J=8Hz), 1.06(s, 3H), 0.92(s, 3H).

Embodiment 2

[0022] Synthesis of Example 2 Compound 1a

[0023]

[0024] 100 g of compound 2a, 150 ml of acetic anhydride and 52 ml of acetic acid were reacted at a pressure of 0.6 MPa and a temperature of 200° C. for 1 hour. Transfer the reaction solution to a distillation flask, recover the unreacted acetic anhydride and acetic acid under reduced pressure, dissolve the residue with 21 g of ethyl acetate, then add 1.2 g of rose bengal, and react for 2.5 hours under incandescent lamp irradiation until all the raw materials are completely reacted. After recovery of ethyl acetate under reduced pressure, 1 l of acetic acid was added, heated to reflux and stirred for 13 hours, and cyclohexane was added for extraction. The cyclohexane extract was washed with saturated sodium bicarbonate water and brine, the solvent was evaporated under reduced pressure, and recrystallized with ethanol to obtain 63 g of compound 1a with a yield of 72%.

Embodiment 3

[0025] Synthesis of Example 3 Compound 4a

[0026]

[0027] 100 g of compound 2a, 150 ml of acetic anhydride and 52 ml of acetic acid were reacted at 0.6 MPa and 200° C. for 1 hour. Transfer the reaction solution to a distillation flask, recover the unreacted acetic anhydride and acetic acid under reduced pressure, dissolve the residue with 21 cyclohexane, then add 0.7 g of tetraphenylporphyrin, react with incandescent lamp for 3 hours and complete the reaction of all raw materials , cyclohexane was distilled off under reduced pressure, and 10.2 g of compound 4a was isolated with a yield of 80%.

[0028] 1 H-NMR (400MHz, CDCl 3 ( m, 1H), 3.95-3.88(m, 2H), 2.74-2.72(d, 1H, J=8Hz), 2.03-2.04(d, 6H), 1.03(s, 3H), 0.94-0.92(d, 3H , J=8Hz), 0.74(s, 3H).

[0029] ESI-Ms: 553.3 [M+Na + ].

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Abstract

The invention relates to a method for synthesizing a pregnenolol acetate and a congener thereof. In the method, a three-step reaction consisting of cracking, oxygen oxidation and rearrangement and elimination is undergone in a 'one-pot' based on steroid sapogenin to obtain the pregnenolol acetate and the congener thereof. By adopting the method, the problem of environmental pollution caused by the use of a metal compound and high-toxicity pyridine hydrochloride is solved in the reaction, and the problem of the harm of high-toxicity solvents, including acetonitrile, benzene and the like to operating personnel is eliminated. The method has the advantages of simple equipment, easiness and convenience for operation, mild condition and high total yield. A more environmentally-friendly and simpler method is provided for the industrial production of pregnenolone acetate.

Description

technical field [0001] The invention relates to a method for synthesizing pregnenol acetate and its congeners. Pregnenone acetate and its analogues are synthesized from steroidal saponins through three-step reactions of cleavage, oxygen oxidation, rearrangement and elimination in a "one-pot" manner. The method eliminates the problem of environmental pollution caused by the use of metal compounds and highly toxic pyridine hydrochloride in the reaction, and also eliminates the problem of poisoning operators caused by the use of highly toxic solvents such as acetonitrile and benzene. The method has the advantages of simple equipment, convenient operation, mild conditions and high total yield, and provides a more environmentally friendly and simpler method for the industrial production of pregnenolone acetate in the future. technical background [0002] Pregnenone alcohol acetate derivatives include a series of pregnen-16-en-20-one compounds, which are important synthetic inter...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J13/00C07J71/00
Inventor 田伟生吴晶晶汪昀史勇
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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