Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzyl azide | HCID 12152 | — |
| Reactant | Sodium Ascorbate | HCID 23667548 | — |
| Reactant | HCID 57899230 | HCID 57899230 | — |
| Catalyst | Copper sulfate pentahydrate | HCID 24463 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | tert-Butanol | HCID 6386 | — |
| Product | HCID 57899244 | HCID 57899244 | 72.3% |
Reaction Steps
To a suspension of (E)-3-[4-(1-but-3-ynyl-pyrrolidin-2-yl)-phenyl]-acrylic acid methyl ester (50 mg, 0.176 mmol) and benzyl azide (23.5 mg, 0.176 mmol) in a mixture of water (0.7 mL) and tert-butanol (0.7 mL) were added a solution of sodium ascorbate (1 M in water, 18 μL) and copper sulfate pentahydrate (4.4 mg). The resulting mixture was stirred vigorously for 16 h, diluted with water, cooled to 0° C., and filtered, and the solid was washed with cold water and dried in vacuo to give (E)-3-(4-{1-[2-(1-benzyl-1H-[1,2,3]triazol-4-yl)-ethyl]-pyrrolidin-2-yl}-phenyl)-acrylic acid methyl ester (53 mg, 72% yield). LCMS (m/z): 417.2 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07943652B2 |
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| Source dataset | uspto-grants-2011_05 |
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| ORD ID | ord-e91a4acddd2f498486da49a32bae1694 |
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| Source note | uspto-grants-2011_05 |
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