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Tetrahydro-2-furoic acid is a low melting solid or high boiling liquid, depending on temperature. Tetrahydro-2-furoic acid is a useful pharmaceutical intermediate and is used in the process to several drugs, including Terazosin for the treatment of prostate enlargement and hypertension.
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Synthesis
Furoic acid was reduced to tetrahydro-2-furoic acid in 1913 by Wienhaus. More recently, tetrahydro-2-furoic acid has been prepared via selective hydrogenation of 2-furoic acid over a bimetallic catalyst of palladium-nickel supported on alumina.
Enantioselective heterogeneous hydrogenation of furoic acid to chiral tetrahydro-2-furoic acid was achieved in the presence of cinchonidine-modified alumina supported palladium catalyst in 95% yield and 32% enantiomeric excess. Similarly, homogeneous hydrogenation to chiral tetrahydro-2-furoic acid was accomplished in 100% yield and 24-27% enantiomeric excess in methanol solution employing a chiral, phosphine modified ferrocene catalyst.
Pharmaceuticals
Reaction of tetrahydro-2-furoic acid with the hydrochloride salt of 3-[(4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino]-propanenitrile provided Alfuzosin, a drug for the treatment of benign prostatic hyperplasia (BPH).
A key intermediate to Faropenem, an antibiotic for the treatment of acute bacterial sinusitis, chronic bronchitis and pneumonia has been prepared from tetrahydro-2-furoic acid via a process including chiral resolution and chlorination.
Tecadenoson is another example of a drug made using tetrahydro-2-furoic acid.