ChemicalBook CAS DataBase List Cilomilast

Cilomilast synthesis

4synthesis methods

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

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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 NO_4.1/8 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