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Synthesis of 13C-labelled medroxyprogesterone acetate with three 13C isotopes [1]

✍ Scribed by P. Narasimha Rao; Kalyani M. Damodaran

Publisher
John Wiley and Sons
Year
1982
Tongue
French
Weight
493 KB
Volume
19
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

17α‐Hydroxyprogesterone (2) was converted to an enol‐lactone 8 in which the 20‐oxo group was selectively protected as an ethylene acetal. The enol‐lactone 8 was subjected to Claisen condensation with phenl acetate‐1,2‐^13^C~2~ in the presence of sodium hydride, which on subsequent treatment with a mixture of acetic acid and hydrochloric acid followed by acetylation gave 17α‐acetoxyprogesterone‐3,4‐^13^C~2~ (9). The enol‐ether 10 obtained from 9 was treated with tetrabromomethane‐^13^C, in pyridine‐dioxane solution, to give the 6‐dibromomethylene derivative 11, Which was then hydrogenated to yield finally 17α‐acetoxy‐6α‐methyl‐^13^C‐pregn‐4‐ene‐3,20‐dione‐3,4‐^13^C~2~ (12).

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