Synthesis of Vigabatrin®.
✍ Scribed by Meng-Yang Chang; Chun-Yu Lin; Chi-Wi Ong
- Book ID
- 101993098
- Publisher
- John Wiley and Sons
- Year
- 2007
- Weight
- 18 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0931-7597
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## Abstract Carbon‐14 labeled vigabatrin was synthesized in 5 steps from 5‐hydroxymethyl‐2‐pyrrolidone tosylate and NaCN‐[^14^C]. A key step involved reduction of the resulting nitrile in the presence of excess dimethylamine to give the dimethylamino‐ethyl 2‐pyrrolidone derivative in one step. This
Vigabatrin-[6-14C] ((R,S)-4-amino-5-hexenoic-[6-14C] acid) was synthesized by employing Wittig condensation of 1-(1- butenyl)-2-oxo-5-pyrolidinecarboxaldehyde with methyl-[ 14C]-triphenylphosphonium iodide as the key step. The synthetic sequence involved 3 steps and produced the title compound in 70