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CAS RN: 1450841-27-6 | Product Number: B4228
2,6-Bis[(2S,5S)-4,4-diphenyl-1-aza-3-oxabicyclo[3.3.0]octan-2-yl]pyridine
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![2,6-Bis[(2S,5S)-4,4-diphenyl-1-aza-3-oxabicyclo[3.3.0]octan-2-yl]pyridine](/_ui/responsive/theme-tci/images/missing_product_zoom.jpg "2,6-Bis[(2S,5S)-4,4-diphenyl-1-aza-3-oxabicyclo[3.3.0]octan-2-yl]pyridine")
Purity: >90.0%(HPLC)
Synonyms:
Product Documents:
| Size | Unit Price | Philadelphia, PA | Portland, OR | Japan* | Quantity |
|---|---|---|---|---|---|
| 50MG |
$136.00
|
Contact Us | Contact Us | 16 |
|
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| Product Number | B4228 |
| Purity / Analysis Method | >90.0%(HPLC) |
| Molecular Formula / Molecular Weight | C__4__1H__3__9N__3O__2 = 605.78 |
| Physical State (20 deg.C) | Solid |
| Storage Temperature | Room Temperature (Recommended in a cool and dark place, <15°C) |
| CAS RN | 1450841-27-6 |
| PubChem Substance ID | 253659536 |
Specifications
| Appearance | White to Light yellow powder to crystal |
| Purity(HPLC) | min. 90.0 area% |
| Specific rotation [a]20/D | -173 to -183 deg(C=1, CHCl3) |
Properties (reference)
| Specific Rotation | -174° (C=1,CHCl3) |
GHS
Related Laws:
Transport Information:
| HS Number | 2934.99.4400 |
Application
An Efficient Bis(oxazolidine)pyridine Ligand Utilizing for the Asymmetric [3+2] Cycloaddition
Experimental Procedure:
Bis(oxazolidine)pyridine ligand (B4228, 0.0165 mmol) and Cu(OAc)2 (0.015 mmol) are added to a round flask containing a stir bar under Ar. CH2Cl2 (1 mL) is added to the flask and the mixture is stirred over 12 hours. To the resulting solution is added azomethine imine (0.15 mmol) at rt. After cooling to –40 °C, to the mixture is added ethyl propiolate (0.18 mmol). After stirring for 47 hours, the reaction mixture is purified by silica gel column chromatography (Et2O/Hexane=2/1 to Et2O) to afford the desired N,N-bicyclic pyrazolidinone derivative (99% yield, 94% ee).
Bis(oxazolidine)pyridine ligand (B4228, 0.0165 mmol) and Cu(OAc)2 (0.015 mmol) are added to a round flask containing a stir bar under Ar. CH2Cl2 (1 mL) is added to the flask and the mixture is stirred over 12 hours. To the resulting solution is added azomethine imine (0.15 mmol) at rt. After cooling to –40 °C, to the mixture is added ethyl propiolate (0.18 mmol). After stirring for 47 hours, the reaction mixture is purified by silica gel column chromatography (Et2O/Hexane=2/1 to Et2O) to afford the desired N,N-bicyclic pyrazolidinone derivative (99% yield, 94% ee).
References
- Development of a tailor-made bis(oxazolidine)pyridine–metal catalyst for the [3+2] cycloaddition of azomethine imines with propiolates
PubMed Literature
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