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| SP - CYANOBOROHYDRIDE RESIN, MP |
| PRODUCT: |
| SP-Cyanoborohydride Resin, MP, a highly cross-linked polystyrene resin functionalized with a tetraalkylammonium cyanoborohydride end group. |
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| APPLICATIONS: |
- SP-Cyanoborohydride resin is a versatile reducing agent used for the reductive amination of carbonyl compounds with primary and secondary amines and reduction of imines.
- SP-Cyanoborohydride is compatible with mild acidic conditions typically used for reductive amination reactions.
- SP-Cyanoborohydride can also be utilized to convert pyridinium ions to tetrahydropyridine derivatives, dehalogenation reactions, and in the reduction of ,-unsaturated carbonyl compounds to the corresponding unsaturated alcohols.
- At the completion of a typical reductive amination reaction, the product amine is present as its acetate salt. Purification of the product amine by “Catch and Release” using SP- Sulfonic Acid generates the free amine and also serves to purify the product amine away from the excess starting carbonyl compound.
- In the case of reductive alkylation using an excess of primary amine, a supported benzaldehyde resin may be used to scavenge the excess starting primary amine from the product secondary amine. Neutralization with SP-Carbonate is then used to generate free amine product from the acetate salt.
- SP-Cyanoborohydride mostly retains the toxic cyanide residue attached to the resin when the reaction is complete minimizing cyanide contamination of the product, which is not the case when using small molecule sodium cyanoborohydride.
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PROPERTIES:
Resin Type: Macroporous poly( styrene-co-divinylbenzene)
Loading: 3.0-2.8 mmol/g (based on titration and elemental analysis)
Bead Size: 325-1225 microns, 15-50 mesh (>90% within) |
| Typical Scavenging: |
Carbonyl compound (1.2 mmol), primary/secondary amine (1.0 mmol) in THF, HOAc (0.25 ml) and SP-Cyanoborohydride (2.0 mmol) stirred overnight at room temperature. Removal of the resin by filtration isolates the product. |
| Compatible Solvents: |
THF, DCM, DMF, MeOH and EtOH |
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| REFERENCES: |
- Habermann, J.; Ley, S.V.; Scott, J.S. J. Chem. Soc. Perkin Trans. 1, 1998 3127.
- Ley, S.V.; Bolli, M.H.;Hinzen B.;Gervois, A-G.;Hall, B.J. J.Chem.Soc.Perkin Trans.1,1998,2239.
- Hutchins, R.O.; Natale, N.R.; Taffer, I.M. J. Chem. Soc. Chem. Commun. 1978, 1088.
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