Selective Thermal Deprotection of N-Boc Protected Amines in Continuous Flow

Monday, 25 March 2024 at 11:00

Add to Calendar ▼2024-03-25 11:00:002024-03-25 12:00:00Europe/LondonSelective Thermal Deprotection of N-Boc Protected Amines in Continuous FlowFlow Chemistry European Summit 2024 in Rotterdam, The NetherlandsRotterdam, The NetherlandsSELECTBIOenquiries@selectbiosciences.com

Among the various protecting groups employed to protect amines during synthetic steps, Boc protection has proved particularly effective. While removal of Boc protecting groups under acidic conditions is one of the most frequently encountered transformations within the chemical and pharmaceutical community, there are limitations including selectivity, compatibility with other acid labile groups, vigorous off-gassing and foaming. Thermal N-Boc deprotection of a range of amines is readily effected in continuous flow, in the absence of an acid catalyst. While the optimum results were obtained in methanol or trifluoroethanol, deprotection can be effected in a range of solvents of different polarities. Sequential selective deprotection of N-Boc groups has been demonstrated, as exemplified by effective removal of an aryl N-Boc group in the presence of an alkyl N-Boc group.

Anita Maguire, Professor of Pharmaceutical Chemistry, University College Cork

Anita Maguire

Anita is a graduate of UCC (BSc 1985, PhD 1989). Following postdoctoral research in Namur, Belgium then in Exeter, UK, Anita returned to UCC in 1991 to establish a research team in synthetic organic chemistry and has played a strategic role at the interface with the pharmaceutical industry. She is a Co-PI in the national SFI Centre SSPC. She was elected as a Member of the Royal Irish Academy in 2014 and appointed RIA Vice President in 2019. She was an Adjunct Professor in the University of Bergen, 2011-16. She was VP Research & Innovation in UCC 2011-21. Throughout her career she has been actively engaged nationally in strategic R&I policy development including as a member of the Advisory Science Council. Since 2015 she is the inaugural Chair of the National Forum on Research Integrity, leading national policy development and implementation in this area.