Cilomilast synthesis
- Product Name:Cilomilast
- CAS Number:153259-65-5
- Molecular formula:C20H25NO4
- Molecular Weight:343.42
![1-Cyclohexene-1-carboxylic acid, 4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]-, methyl ester](/CAS/20210305/GIF/153259-59-7.gif)
153259-59-7
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153259-65-5
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Yield:153259-65-5 54%
Reaction Conditions:
palladium on activated carbon in methanol;
Steps:
3 Procedure 3A:
EXAMPLE 3 Methyl cis- and trans-[4-cyano4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexane-1-carboxylate] Procedure 3A: To a solution of methyl 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohex-1-ene-1-carboxylate (0.26 g, 0.73 mmol) in methanol (12 mL) was added 10% palladium on activated carbon (0.15 g) and the resulting mixture was hydrogenated at 50 psi for 5 h. The mixture was filtered through a pad of Celite and concentrated under reduced pressure. The residue was partitioned between methylene chloride and water, the extract was dried (potassium carbonate) and evaporated to a solid which was primarily the cis-ester (0.14 g, 54%): m.p. 94°-95° C. Analysis Calc. for C21 H27 NO4.1/8 H2 O: C 70.32, H 7.38, N 3.90; found: C 70.33, H 7.59, N 3.81.
References:
US5602157,1997,A
![Cyclohexanecarboxylic acid, 4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]-, methyl ester, cis-](/CAS/20210305/GIF/153259-61-1.gif)
153259-61-1
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153259-65-5
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![1-[3-(CYCLOPENTYLOXY)-4-METHOXYPHENYL]-4-OXOCYCLOHEXANE-1-CARBONITRILE](/CAS/GIF/152630-47-2.gif)
152630-47-2
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153259-65-5
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![Cyclohexanecarbonitrile, 1-[3-(cyclopentyloxy)-4-methoxyphenyl]-4-(1,3-dithian-2-ylidene)-](/CAS/20210305/GIF/153260-05-0.gif)
153260-05-0
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153259-65-5
117 suppliers
$28.00/1mg