A convenient synthesis of N-boc protected primary amines via the reaction of organoboranes with Li or K t-butyl-N-tosyloxycarbamate

Jean-Pierre Genet (1) , Josef Hajicek , Laurent Bischoff (2) , Christine Greck (3)

1 SSOPN - Synthèses sélective organique et produits naturels
2 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
3 ILV - Institut Lavoisier de Versailles

Primary and secondary alkylboranes reacted rapidly at low temperature with Li or K t-butyl-N-tosyloxycarbamate (LiBTOC or KBTOC) to give the corresponding N-Boc protected primary amines in modest to good yields (16–81%). N-Boc primary amines were obtained from the reaction of alkylboranes with Lithium or Potassium salts of t-butyl-N-tosyloxycarbamate.

Keywords: Amination; Organoboranes; t-Butyl-N-tosyloxycarbamate

Domains: Chemical Sciences; Chemical Sciences; Organic chemistry; Chemical Sciences; Medicinal Chemistry; Chemical Sciences; Radiochemistry; Chemical Sciences; Material chemistry; Chemical Sciences; Inorganic chemistry; Chemical Sciences; Catalysis

Jean-Pierre Genet, Josef Hajicek, Laurent Bischoff, Christine Greck. A convenient synthesis of N-boc protected primary amines via the reaction of organoboranes with Li or K t-butyl-N-tosyloxycarbamate. Tetrahedron Letters, 1992, 33 (19), pp.2677-2680. ⟨10.1016/S0040-4039(00)79055-1⟩. ⟨hal-02385498⟩