Removal of a primary Boc group under basic conditions

30 April 2004

Workers at Pfizer have found that Boc-protected primary amines can be deprotected under basic conditions if a strong base is used. In a typical reaction 2-4 equivalents of sodium tert -butoxide is added to a solution of 1 equivalent of the primary amine in 10 volumes of THF. 1 equivalent of water is added and the reaction is heated at reflux for 2-12 hours. Yields are >90%. An isocyanate intermediate is postulated, and this is supported by the fact that secondary amines are recovered unchanged.

Tetrahedron Letters , 2004 , 45(5) , 905-6.