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Synthesis and NMR-analysis of deuterated and tritiated cyclooctyl acetic acid

✍ Scribed by Frans M. Kaspersen; Irene H. G. Schlachter; Carel W. Funke; Gerard N. Wagenaars; Jan-Remt Mellema

Publisher
John Wiley and Sons
Year
1991
Tongue
French
Weight
129 KB
Volume
29
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

To increase the bio‐availability of naturally occurring steroids, esterification of the 17‐hydroxy position is a useful approach. Besides (branched) alkanecarboxylic acids^1^) and cyclohexanecarboxylic acid^2^) also cyclooctyl acetic acid (1) was applied. To establish the biological fate of the cyclooctyl acetic acid part of steroids the tritiated molecule was synthesized (Figure 1). Cyclooctanone (3) was condensed with cyanoacetic acid^3^) and the resulting cyanide (4) was hydrolyzed to cyclooctenyl acetic acid (2a)^4^) which contained according to ^1^H NMR and ^13^C NMR 20% of the isomeric 2b(^1^H NMR (C^2^HCl~3~): 5,58 ppm (t, CH of 2a) and 5,63 ppm (br.s CH of 2b) ^13^C NMR(C^2^HCl~3~): 129,6 ppm (CH of 2a) and 115,0 ppm (CH of 2b)).

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