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| SP-BOROHYDRIDE RESIN, MP |
| PRODUCT: |
| SP-Borohydride Resin, MP, a highly cross-linked polystyrene resin functionalized with a tetraalkylammonium borohydride end group. |
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| APPLICATIONS: |
- SP-Borohydride resin is a versatile reducing agent used for the reductive amination of carbonyl compounds with primary and secondary amines.
- SP-Borohydride can also be used in conjunction with titanium (IV) isopropoxide for reductive amination of aldehydes and ketones. Titanium (IV) isopropoxide may be conveniently scavenged using SP-Aminopolyhydroxy resin. The reductive amination products can be purified by “Catch and Release” of the amines using SP-Sulfonic Acid.
- SP-Borohydride can be used for the reduction of aldehydes, ketones and imines.
- The resin can also be used for other important reductive applications such as reduction of oximes, azides and alkyl halides, in conjunction with some transition metal salts.
- The products are isolated from the resin by simple filtration.
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PROPERTIES:
Resin Type: Macroporous poly(styrene-co-divinylbenzene)
Loading: 3.0-2.7 mmol/g (based on hydrogen gas evolution on treatment with aqueous acid)
Bead Size: 325-1225 microns, 15-50 mesh (>90% within) |
Scavenging Aldehyde or
Ketone reduction: |
Carbonyl compound (1.0 mmol) in MeOH or EtOH and SP-Borohydride (1.0
mmol) stirred at ambient temperature for 3-10 h. Reaction time varies on the nature of the carbonyl compound. Removal of the resin by filtration isolates the product, generally in high purity. |
| Compatible Solvents: |
THF, DCM, MeOH, EtOH and DMF |
| Storage and Stability: |
The resin should be stored at 4 C, has been found to be stable for more than 4 months, in ongoing stability studies. |
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| REFERENCES: |
- Habermann, J.; Ley, S. V.; Scott, J.S. J. Chem. Soc. Perkin Trans. 1. 1999, 1253.
- Ley, S. V; Schucht, O.; Thomas, A. W.; Murray, J.P. J. Chem. Soc. Perkin Trans. 1, 1999, 1251.
- Yoon, N. M.; Choi, J.; Ahn, J.H. .J. Org. Chem. 1994, 59, 3490.
- Kabalka, G. W; Wadgaonkar, P. P.; Chatla, N. Synth. Commun. 1990, 20, 293.
- Yoon, N. M.; Park, K. B.; Gyoung, Y. S. Tetrahedron Lett. 1983, 24, 5367.
- Gibson, H. W.; Bailey, F. C. J. Chem. Soc. Chem. Commun. 1977, 815.
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