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| SP-DIISOPROPYLETHYLAMINE RESIN (DIEA), MP |
| PRODUCT: |
| SP -Diisopropylethylamine Resin, MP, a highly cross-linked polystyrene resin functionalized with a non-nucleophilic base, diisopropylethylamine, also called Huenig’s base end group. |
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| APPLICATIONS: |
- SP-DIEA can be used in applications requiring a tertiary amine base and where the resin-bound ammonium salt byproducts are readily separated by filtration.
- One pot synthesis of amides, sulfonamides and carbamates can be effected using filtration as the only purification step when SP-DIEA is used in conjunction with SP-Trisamine as a scavenger resin.
- SP-DIEA is linked to the polystyrene backbone through the benzylic position by analogy to other resin-bound amine bases, e.g. morpholinomethyl polystyrene.
- The increased steric hindrance associated with the diisopropyl substitution affords a significantly more stable benzylic tertiary amine base, even in the presence of reactive electrophiles like chloroformates.
- SP-DIEA has a highly cross-linked macroporous resin backbone, hence SP-DIEA is not dependent on swelling to be effective, making it compatible with a broad range of solvents including highly polar solvents.
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PROPERTIES:
Resin Type: Macroporous Poly(styrene-co-divinylbenzene)
Loading: 2.8 - 2.4 mmol/g (based on nitrogen analysis)
Bead Size: 330-1225 microns, 15-50 mesh (>90% within) |
| Conditions: |
2-3 equiv relative to limiting reagent |
| Compatible Solvents: |
DCM, THF, DMF, acetonitrile |
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| REFERENCES: |
- Bhattacharyya, S.; Fan, L.; Vo, L.; Labadie, J. Combi Chem & High Throughput Screen, 2000, 3, 117.
- Conti, P.; Demont, D.; Cals, J.; Ottenheijm, H. C. J.; Leysen, D. Tetrahedron Lett 1997, 38, 2915.
- Booth, R. J.; Hodges, J.C. J. Am. Chem. Soc 1997, 119, 4882.
- Yang, B. V.; O' Roarke, D.; Li J. Synlett 1993, 195.
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