For over 15 years Biotage has been guiding and leading the industry in supported reagents and scavengers.
Biotage® PS-TsNHNH2 is a resin-bound equivalent of p-toluenesulfonyl hydrazide and is an excellent scavenger of aldehydes and ketones. Comparison with other polymeric benzyl hydrazide showed PS-TsNHNH2 was a superior scavenger for carbonyls and much more stable to storage (other benzyl hydrazide resins decomposed on storage).
Removal of excess carbonyls from solution generally requires upto a three-fold excess of PS-TsNHNH2. Addition of a catalytic amount of HOAc (5–10%) may be required for ketones and hindered aldehydes. HOAc is also required for sequestering aldehydes in DMF. Complete removal of common aldehydes occurs in 0.5 to 3 h and removal of a ketone takes from 2 to 16 h. Elevated temperatures were required for hindered ketones (e.g. 2,6-dimethylcyclohexanone). Upon completion of the scavenging, the resin is rinsed with a suitable solvent (i.e. those which swell polystyrene), and the product is isolated by concentration.
Application to Grignard Reactions
PS-TsNHNH2 was successfully used to work up the synthesis of alcohols by addition of a Grignard reagent to aldehydes. PS-TsNHNH2 is also potentially useful as a polymer-supported reagent. Supported sulfonyl hydrazones, formed by condensation with carbonyl compounds, can be utilized in further synthetic transformations. The high accessibility of tosyl hydrazide functional groups in PS-TsNHNH2 afford high synthetic fidelity relative to reported systems.
This scavenger can be applied to the rapid clean-up of tertiary amines prepared through reductive amination using MP-Triacetoxyborohydride and microwave irradiation.
Inert, specifically-reactive and deployed to achieve a specific purpose. With lot control, QA / QC documentation, SDS, ISO 9001 / 14001 registration, BSE / TSE statement, shelf-life statement, these resins also support the audit trail.
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Biotage is headquartered in Uppsala in Sweden and employs more than 500 people worldwide. The Group had sales of 1,092 MSEK in 2020 and our products are sold in more than 70 countries. Biotage’s share (BIOT) is listed in the Mid Cap segment on the NASDAQ Stockholm.