Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Cyclopropylacetylene | HCID 138823 | — |
| Reactant | Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate | HCID 10991161 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 86732160 | HCID 86732160 | — |
Reaction Steps
A RT mixture of tert-butyl 4-(((trifluoromethyl)sulfonyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate (0.750 g, 2.264 mmol), trans-dichlorobis(triphenylphosphine)palladium (II) (0.081 g, 0.115 mmol) and copper (I) iodide (0.023 g, 0.121 mmol) in toluene (10 mL) was bubbled with argon for 15 min. cyclopropylacetylene (0.600 ml, 7.08 mmol, Aldrich) and triethylamine (0.350 ml, 2.52 mmol) were added resulting in a brown mixture after 5 min. The reaction mixture was partitioned between CH2Cl2/water and the aqueous layer was extracted with CH2Cl2 (3×). The combined organic layers were washed with brine and dried over MgSO4. The solution was filtered and the filtrate was evaporated onto silica gel and purified by flash chromatography (Isco (80 gram)) eluting with (EtOAc):hexanes (0:1→1:9) to give tert-butyl 4-(cyclopropylethynyl)-5,6-dihydropyridine-1(2H)-carboxylate as a yellow tar (344 mg, 61%). MS m/z=192 [M+H-tBu]+. Calculated for C11H13NO2: 191
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09296734B2 |
|---|
| Source dataset | uspto-grants-2016_03 |
|---|
| ORD ID | ord-02887cfb6c584f4fabe8b36aedf30fd3 |
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| Source note | uspto-grants-2016_03 |
|---|
