The Mono-Boc protection of p-xylylenediamine in the Africa flow microreactor
Date Posted: Monday, December 17, 2007
Microreactors offer rapid chemical optimisation coupled with minimal use of starting materials. The experiment described, vide infra, is part of a one day investigation into the synthesis optimisation of N-Boc-p-xylylenediamine.
The tert-butyloxycarbonyl group (Boc) is one of the most commonly used amine protecting groups. It is non-labile to catalytic hydrogenation, basic conditions and other nucleophiles. Deprotection is subsequently performed by acids like HCl and trifluoroacetic acid (TFA).
Diamines have application as a spacer group moiety and when used in asymmetric molecules it is often necessary to protect one of the amino groups.
The synthesis of mono-protected p-xylylenediamine involves the addition of (Boc)2O to thediamine, with the crude reaction mixture containing: mono-protected p-xylylenediamine, diprotected p-xylylenediamine, and unreacted p-xylylenediamine
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