SINTESIS 16-DEHIDROPREGNENOLON ASETAT

• Main Author: Nashrianto, Husain
• Format: Theses
• Language: Indonesia
• Online Access: https://digilib.itb.ac.id/gdl/view/1177
• Institution: Institut Teknologi Bandung

In the production of steroid hormones,16-dehydropregnenolone acetate (16-DPA) is an intermediate and as such can also be considered as a raw material for the hormone production. The synthesis of this 16-DPA was endeavoured both as a one stage and as a two - stage operation. In the two-stage operation using 3.8 mole equivalent acetic anhydride in pyridine for acetylation to 0,N-diacetylsolasodine, the result could be isolated over alumina column with eluent benzene - ether ( 1 : 1 ) and yielded 77.5% of the 0,N - diacetylsolasodine, mp 163 - 166°C. In the next stage boiling glacial acetic acid was added to produce the 0,N - diacetyipseudosolasodine, which was again isolated through an alumina column and eluted with 0.5% methanol in ether. This stage gave a 73.7% yield, mp 132-137° C. Then in the oxidation stage using Crom (VI) oxide, the diketone compound was produced followed by Cuttingoff of the acyloxy side chain by hydrolysis using acetic acid. A white crystalline solid of 16-dehydropregnenolone acetate with 55% yield, trip 168-173°C was obtained. In the one - stage operation without purification or isolation of the intermediates, an over-all yield of0.1% of the 16-dehydropregnenolone acetate, mp 168-173°C was obtained. Spectroscopic data included 1R, IH-NMR, UV, and mass spectra of expected compounds were also reported.