Tetrahydro-2-furoic acid is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula HO₂CC₄H₇O. It is a colorless oil. Tetrahydro-2-furoic acid is a useful pharmaceutical intermediate relevant to the production of several drugs, including

Terazosin Terazosin, sold under the brand name Hytrin among others, is a medication used to treat symptoms of an enlarged prostate and high blood pressure Hypertension (HTN or HT), also known as high blood pressure (HBP), is a long-term medical con ...

for the treatment of prostate enlargement and hypertension. or high boiling liquid,

Synthesis

Furoic acid is reduced to tetrahydro-2-furoic acid, as originally reported in 1913 by Wienhaus. 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 proceeds 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 proceeds quantitatively with 24-27% enantiomeric excess in methanol solution employing a chiral, ferrocene-phosphine catalyst.

Applications

Pharmaceuticals

Reaction of tetrahydro-2-furoic acid with the hydrochloride salt of 3- 4-amino-6,7-dimethoxy-2-quinazolinyl)methylaminopropanenitrile provided

alfuzosin Alfuzosin, sold under the brand names Alfosoft and Uroxatral, among others, is a medication of the α1 blocker class. It is used to treat benign prostatic hyperplasia (BPH). As an antagonist of the α1 adrenergic receptor, it works by relax ...

, a drug for the treatment of

benign prostatic hyperplasia Benign prostatic hyperplasia (BPH), also called prostate enlargement, is a noncancerous increase in size of the prostate gland. Symptoms may include frequent urination, trouble starting to urinate, weak stream, inability to urinate, or loss o ...

(BPH). A key intermediate to

faropenem Faropenem is an orally active beta-lactam antibiotic belonging to the penem group. It is resistant to some forms of extended-spectrum beta-lactamase. It is available for oral use. Forms Faropenem was developed by Daiichi Sankyo, Daiichi Asubio ...

, 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.

References

{{Reflist, 2 Tetrahydrofurans Carboxylic acids