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US 6,683,197 B1Granted
Process for the production of 4,4-dimethyl-5α-cholesta-8,14,24-trien-3β-01 and intermediate products in process (I)
AssigneeSchering Corporation
InventorsThorsten Blume, Peter Esperling, Joachim Kuhnke
Life of this patent
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Abstract
The subject of this invention is a new process with variant embodiments for the production of compound 1.
Claims6
A process for the production of 4,4-dimethyl-5α-cholesta-8,14,24-trien-3β-ol of formula 1
- comprising:
- a) reacting a 3-oxopregn-4-enoic-21-acid ester of formula 2
- in which
- R1 means hydrogen, branched or unbranched C1-C6 alkyl;
- phenyl;
- benzyl;
- ortho-, meta- or para-methylphenyl,
- in the presence of a base and a methylating agent to produce a compound of formula 3
- in which
- R1 has the above-mentioned meaning,
- b) reducing the compound of formula 3 to a compound of formula 4
- in which
- R1 has the above-mentioned meaning,
- c) converting the 3-hydroxy group of the compound of formula 4 into a 3-protected hydroxy group of the compound of formula 5
- in which
- R1 has the above-mentioned meaning, and
- R2 means hydrogen, an ester of an aliphatic or an aromatic carboxylic acid, an acetal protective group, or a silyl ether,
- d) dehydrogenating the compound of formula 5 into a compound of formula 6
- in which
- R1 and R2 have the above-mentioned meanings,
- e) isomerizing the compound of formula 6 into a compound of formula 7
- in which
- R1 and R2 have the above-mentioned meaning,
- f) alkylating the compound of formula 7 into a compound of formula 8
- in which
- R1 and R2 have the above-mentioned meaning,
- g) reducing the ester of the compound of formula 8 into a hydroxymethyl group of a compound of formula 9
- in which
- R2 has the above-mentioned meaning,
- h) converting the primary hydroxyl group in a leaving group of the compound of formula 9 into a compound of formula 10
- in which
- R2 has the above-mentioned meaning, and
- R3 stands for radical SO2R4, whereby R4 means branched or unbranched C1-C6 alkyl;
- phenyl;
- benzyl;
- ortho-, meta- or para-methylphenyl or 2,4,6-trimethylphenyl,
- and, if R2 is hydrogen, the direct reaction of a compound of formula 10 into 4,4-dimethyl-5α-cholesta-8,14,24-trien-3β-ol of formula 1,
- i) or if R2 is a protective group by reductive removal of the —OR3 grouping into a compound of formula 11
- in which
- R2 has the above-mentioned meaning, and and cleavage of the protective group.
37 more elements
A process for the production of 4,4-dimethyl-5α-cholesta-8,14,24-trien-3β-ol of formula 1
- comprising:
- isomerizing a compound of formula 6
- R1 means hydrogen, branched or unbranched C1-C6 alkyl;
- phenyl;
- benzyl;
- ortho-, meta- or para-methylphenyl,
- R2 means hydrogen, an ester of an aliphatic or an aromatic carboxylic acid, an acetal protective group, or a silyl ether.
4 more elements
A process for the production of 4,4-dimethyl-5α-cholesta-8,14,24-trien-3β-ol of formula 1
- comprising:
- dehydrogenating a compound of formula 5:
- to produce a compound of formula 6
- R1 means hydrogen, branched or unbranched C1-C6 alkyl;
- phenyl;
- benzyl;
- ortho-, meta- or para-methylphenyl,
- R2 means hydrogen, an ester of an aliphatic or an aromatic carboxylic acid, an acetal protective group, or a silyl ether.
5 more elements
Compounds of general formula 6
- in which
- R1 means hydrogen, branched or unbranched C1-C6 alkyl;
- phenyl;
- benzyl;
- ortho-, meta- or para-methylphenyl and
- R2 means hydrogen, esters of aliphatic and aromatic carboxylic acids, or silyl ethers.
3 more elements
Dependencies are inferred from the claim text.