A. Kale, V. Puranik, A. Deshmukh
Apr 1, 2007
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Influential Citations
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Journal
Synthesis
Abstract
A practical synthesis of (3 S,6 R)-1,3-dibenzyltetrahydro-1 H-furo[3,4- D]imidazole-2,4-dione, an important intermediate in the synthesis of biotin, from 4-formyl-3-mesyloxyazetidin-2-one has been achieved. Acid-catalyzed azetidin-2-one ring opening followed by a one-pot conversion of diamine hydrochloride to a cyclic urea and hydroxymethylene to chloromethylene by triphosgene to obtain (4 S,5 R)-methyl-1,3-dibenzyl-5-chloromethyl-2-oxoimidazolidine-4-carboxylate is the key step in this synthesis.