(156e) A Quantitative Assay of Sodium Triacetoxyborohydride

Sodium triacetoxyborohydride (STAB) is a common reducing agent for reductive amination reactions. Due to sensitivities to water and air, the potency of this reagent tends to degrade over time. Traditional analytical assays for STAB fail to accurately assess the content of the active borohydride species, and often report assay purities of 97% or greater, when the true potency is lower. An incorrect or unknown potency of the STAB being used may lead to significant challenges when scaling up reductive aminations. An excess of STAB may be required and reactions may not achieve full conversion with the amount of STAB charged, requiring additional charges. The use of an excess of STAB comes with greater raw material costs and the thermal and H₂ evolution hazards associated with quenching the excess reagent.

This presentation outlines a simple assay, based on an aldehyde reduction, that was developed to determine the active borohydride content of STAB. The HPLC assay yield of a salicylaldehyde reduction has been shown to accurately determine this potency and has been validated against an H₂ evolution method, as well as yields obtained from a reductive amination.