title: Scalable synthesis of 1-bicyclo[1.1.1]pentylamine via a hydrohydrazination reaction.
abstract: The reaction of [1.1.1]propellane with di-tert-butyl azodicarboxylate and phenylsilane in the presence of Mn(dpm)(3) to give di-tert-butyl 1-(bicyclo[1.1.1]pentan-1-yl)hydrazine-1,2-dicarboxylate is described. Subsequent deprotection gives 1-bicyclo[1.1.1]pentylhydrazine followed by reduction to give 1-bicyclo[1.1.1]pentylamine. The reported route marks a significant improvement over the previous syntheses of 1-bicyclo[1.1.1]pentylamine in terms of scalability, yield, safety, and cost.
authors.affiliation: Pfizer Worldwide Research and Development, La Jolla Laboratories, 10770 Science Center Drive, San Diego, California 92121, USA. kevin.bunker@pfizer.com
authors.forename: Kevin D
authors.initials: KD
authors.lastname: Bunker
authors.forename: Neal W
authors.initials: NW
authors.lastname: Sach
authors.forename: Qinhua
authors.initials: Q
authors.lastname: Huang
authors.forename: Paul F
authors.initials: PF
authors.lastname: Richardson
mesh_terms: D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006830:Hydralazine / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: C568027:1-bicyclo(1.1.1)pentylamine; D000588:Amines; D001643:Bridged Bicyclo Compounds; D006830:Hydralazine