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Synthesis of 17α ‐ethynylestradiol‐6, 7‐ 3 H and 17α‐ethynylestradiol‐6,7‐ 3 H, 3‐cyclopentyl‐1‐ 14 C ether
Author(s) -
Merrill E. J.,
Vernice G. G.
Publication year - 1970
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590060307
Subject(s) - ether , bromide , estrone , chemistry , tritium , radiochemistry , catalysis , organic chemistry , biochemistry , hormone , physics , nuclear physics
Several authors have reported on the physiological differences between 17α‐ethynylestradiol and its 3‐cyclopentyl ether. The radiolabeled steroids were required to compare their relative absorptions, excretions, and metabolic products. Tritium was introduced into the steroid nucleus by catalytic tritiation of 6‐dehydroestrone. Etherification with either cyclopentyl bromide or cyclopentyl‐ 14 C p‐bromobenzenesulfonate gave the cyclopentyl ether of estrone. Ethynylation of either estrone‐6, 7‐ 3 H or its cyclopentyl‐ 14 C ether gave 17α‐ethynylestradiol‐6, 7‐ 3 H and 17α‐ethynylestradiol‐6, 7‐ 3 H, 3‐cyclopentyl‐ 14 C ether. It was also possible to etherify 17α‐ethynylestradiol directly although in poorer yields.