title: A new route to bicyclo[1.1.1]pentan-1-amine from 1-azido-3-iodobicyclo[1.1.1]pentane.
abstract: From a medicinal chemistry perspective, bicyclo[1.1.1]pentan-1-amine (1) has served as a unique and important moiety. Synthetically, however, this compound has received little attention, and only one scalable route to this amine has been demonstrated. Reduction of an easily available and potentially versatile intermediate, 1-azido-3-iodobicyclo[1.1.1]pentane (2), can offer both a flexible and scalable alternative to this target. Herein, we describe our scrutiny of this reportedly elusive transformation and report our ensuing success with this endeavor.
authors.affiliation: Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology, and Research (A*STAR), 11 Biopolis Way, Helios Block, #03-08, Singapore 138667, Singapore.
authors.forename: Yi Ling
authors.initials: YL
authors.lastname: Goh
authors.forename: Eric K W
authors.initials: EK
authors.lastname: Tam
authors.forename: Paul H
authors.initials: PH
authors.lastname: Bernardo
authors.forename: Choon Boon
authors.initials: CB
authors.lastname: Cheong
authors.forename: Charles W
authors.initials: CW
authors.lastname: Johannes
authors.forename: Anthony D
authors.initials: AD
authors.lastname: William
authors.forename: Vikrant A
authors.initials: VA
authors.lastname: Adsool
mesh_terms: D000588:Amines / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006847:Hydrocarbons, Iodinated / Q000737:chemistry*; D015394:Molecular Structure; D010420:Pentanes / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: C000588837:1-azido-3-iodobicyclo(1.1.1)pentane; D000588:Amines; D001386:Azides; D001643:Bridged Bicyclo Compounds; D006847:Hydrocarbons, Iodinated; D010420:Pentanes; C000588836:bicyclo(1.1.1)pentan-1-amine