CA2568510A1 - One-pot processes for preparing prednisolone derivatives - Google Patents

One-pot processes for preparing prednisolone derivatives Download PDF

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Publication number
CA2568510A1
CA2568510A1 CA 2568510 CA2568510A CA2568510A1 CA 2568510 A1 CA2568510 A1 CA 2568510A1 CA 2568510 CA2568510 CA 2568510 CA 2568510 A CA2568510 A CA 2568510A CA 2568510 A1 CA2568510 A1 CA 2568510A1
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Prior art keywords
formula
compound
process according
molar ratio
catalyst
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Granted
Application number
CA 2568510
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French (fr)
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CA2568510C (en
Inventor
Minghua Ying
Dingwei Wu
Hongpeng Chen
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Zhejiang Xianju Pharmaceutical Co Ltd
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Zhejiang Xianju Pharmaceutical Co Ltd
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Priority to CA002568510A priority Critical patent/CA2568510C/en
Publication of CA2568510A1 publication Critical patent/CA2568510A1/en
Application granted granted Critical
Publication of CA2568510C publication Critical patent/CA2568510C/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

Disclosed is a one-pot process for the preparation of a prednisolone derivative of formula I, comprising reacting the compound of formula II with the compound of formula III and the compound of formula IV The process does not need to separate and purify the intermediate formed, and therefore the process reduces the reaction time and increases th e yield of the product compared to the prior art. (see above formula)

Claims (20)

1. A one-pot process for the preparation of a prednisolone derivative of formula I, wherein R1 represents alkyl, alkenyl, alkynyl, cycloalkyl or aryl; and R2 represents alkyl, alkenyl or alkynyl, comprising reacting the compound of formula II, with a compound of formula III, wherein R2 is as previously defined, and a compound of formula IV, wherein R1 is as previously defined.
2. ~The process according to Claim 1, wherein R1 represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl or C5-C20 aryl.
3. ~The process according to Claim 2, wherein R1 is n-butyl, isobutyl, cyclohexyl or phenyl.
4. ~The process according to Claim 1, wherein R2 represents C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl.
5. ~The process according to Claim 4, wherein R2 is methyl or isopropyl.
6. ~The process according to Claim 1, wherein R1 represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl or C5-C20 aryl, and R2 represents C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl.
7. ~The process according to Claim 6, wherein R1 is n-butyl, isobutyl, cyclohexyl or phenyl, and R2 is methyl or isopropyl.
8. ~The process according to Claim 1, wherein a molar ratio of the compound of formula II, the compound of formula III and the compound of formula IV is 1:1-15:1-10.
9. ~The process according to Claim 8, wherein the molar ratio is 1:4-8:2-6.
10. ~The process according to Claim 1, wherein the process is carried out at the temperature of 0-50°C.
11. ~The process according to Claim 10, wherein the process is carried out at the temperature of 20-30°C.
12. ~The process according to Claim 1, wherein the process is carried out at the presence of a protonic acid catalyst.
13. ~The process according to Claim 12, wherein the protonic acid catalyst is selected form the group consisting of hydrochloric acid, sulfuric acid, perchloric acid, methanesulfonic acid, toluene-p-sulfonic acid and tetrafluoroboric acid.
14. ~The process according to Claim 13, wherein the protonic acid catalyst is a 35-70%
perchloric acid.
15. ~The process according to Claim 14, wherein the protonic acid catalyst is a 60-70%
perchloric acid.
16. ~The process according to Claim 12, wherein a molar ratio of the protonic acid catalyst to the compound of formula II is 1-10:1.
17. ~The process according to Claim 16, wherein the molar ratio of the protonic acid catalyst to the compound of formula II is 1-4:1.
18. ~The process according to Claim 1, wherein the process is carried out at the presence of a polar organic solvent selected from the group consisting of dioxane, methylene chloride, chloroform, nitromethane and ethyl acetate.
19. ~A one-pot process for the preparation of a prednisolone derivative of formula I, wherein R1 is n-butyl, isobutyl, cyclohexyl or phenyl; and R2 is methyl or isopropyl, comprising reacting the compound of formula II, with a compound of formula III, wherein R2 is as previously defined, and a compound of formula IV, wherein R1 is as previously defined, at the presence of dioxane and a catalyst of 60-70% perchloric acid, and at the temperature of 20-30°C, and wherein a molar ratio of the compound of formula II, the compound of formula III and the compound of formula IV is 1:4-8:2-6, and a molar ratio of the catalyst to the compound of formula II is 1-4:1.
20. ~The process according to Claim 19, wherein the catalyst is a 70%
perchloric acid, and the molar ratio of the compound of formula II, the compound of formula III and the compound of formula IV is about 1:6:4, and the molar ratio of the catalyst to the compound of formula II is about 3.8:1.
CA002568510A 2006-11-21 2006-11-21 One-pot processes for preparing prednisolone derivatives Active CA2568510C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA002568510A CA2568510C (en) 2006-11-21 2006-11-21 One-pot processes for preparing prednisolone derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CA002568510A CA2568510C (en) 2006-11-21 2006-11-21 One-pot processes for preparing prednisolone derivatives

Publications (2)

Publication Number Publication Date
CA2568510A1 true CA2568510A1 (en) 2008-05-21
CA2568510C CA2568510C (en) 2009-12-15

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Family Applications (1)

Application Number Title Priority Date Filing Date
CA002568510A Active CA2568510C (en) 2006-11-21 2006-11-21 One-pot processes for preparing prednisolone derivatives

Country Status (1)

Country Link
CA (1) CA2568510C (en)

Also Published As

Publication number Publication date
CA2568510C (en) 2009-12-15

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