14185-28-5Relevant academic research and scientific papers
Continuous and convergent access to vicinyl amino alcohols
Nobuta, Tomoya,Xiao, Guozhi,Ghislieri, Diego,Gilmore, Kerry,Seeberger, Peter H.
, p. 15133 - 15136 (2015/10/12)
Five active pharmaceutical ingredients (APIs) containing the vicinyl amino alcohol moiety were synthesized using a convergent chemical assembly system. The continuous system is composed of four flow reaction modules: biphasic oxidation, Corey-Chaykovsky epoxidation, phenol alkylation, and epoxide aminolysis. Judicious choice of reagents and module order allowed for two classes of β-amino alcohols, aryl and aryloxy, to be synthesized in good (27-69%) overall yields.
One-pot synthesis of N-substituted β-amino alcohols from aldehydes and isocyanides
Cioc, R?zvan C.,Van Der Niet, Daan J. H.,Janssen, Elwin,Ruijter, Eelco,Orru, Romano V.A.
supporting information, p. 7808 - 7813 (2015/05/20)
A practical two-stage one-pot synthesis of N-substituted β-amino alcohols using aldehydes and isocyanides as starting materials has been developed. This method features mild reaction conditions, broad scope, and general tolerance of functional groups. Based on a less common central carbon-carbon bond disconnection, this protocol complements traditional approaches that involve amines and various carbon electrophiles (epoxides, α-halo ketones, β-halohydrins). Medicinally relevant products can be prepared in a concise and efficient way from simple building blocks, as demonstrated in the synthesis of the antiasthma drug salbutamol. Upgrading the synthesis to an enantioselective variant is also feasible.
Asymmetric synthesis of β-amino alcohols by the transfer hydrogenation of α-keto imines
Tafelska-Kaczmarek, Agnieszka,Prewysz-Kwinto, Andrzej,Skowerski, Krzysztof,Pietrasiak, Katarzyna,Kozakiewicz, Anna,Zaidlewicz, Marek
experimental part, p. 2244 - 2248 (2010/11/03)
The asymmetric transfer hydrogenation of representative aryl and benzofuranyl 2-tert-butylaminoethanones with formic acid-triethylamine, catalyzed by RhCl[(R,R)-TsDPEN](C5Me5), produced the corresponding β-tert-butylamino alcohols in 97-99% ee. A short asymmetric synthesis of (R)-bufuralol, a potent β-adrenergic receptor antagonist, is described. This approach to β-amino alcohols from ketones circumvents the halogenation-reduction-amination sequence.
