6-Hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

Uses

6-Hydroxy-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic Acid is useful chemical in the studying of proline containing peptides as caspase-2 inhibitors.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 27, p. 1321, 1984 DOI: 10.1021/jm00376a017

Synthesis

GENERAL PROCEDURE: A solution of 2-oxoacetic acid monohydrate (2.0 g, 22 mmol) in ethanol (10 mL) was added slowly and dropwise to a denatured ethanol (70 mL) solution of 3-hydroxyphenylethylamine hydrochloride (3.08 g, 22.5 mmol) at 4 °C. Immediately after the dropwise addition, a white precipitate was observed to be generated. The ice bath was removed and the reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the white solid product 6-hydroxy-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (3.1 g, 73% yield) was collected by filtration. The product was analyzed by LC/MS (electrospray, positive ion mode) and showed m/z 194 ([M+H]+).

References

[1] Journal of Medicinal Chemistry, 1984, vol. 27, # 10, p. 1321 - 1325
[2] Patent: US6649606, 2003, B1. Location in patent: Page/Page column 38
[3] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 47 - 50
[4] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 7, p. 1799 - 1802