Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Piperidine | HCID 8082 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | (4S,5R)-Tert-butyl 4-(fluoromethyl)-5-(4-iodophenyl)-2,2-dimethyloxazolidine-3-carboxylate | HCID 73424774 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Dichlorobis(triphenylphosphine)palladium | HCID 6102075 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 58631179 | HCID 58631179 | 88.4% |
Reaction Steps
To a toluene (40 ml) solution of (4S,5R)-tert-butyl 4-(fluoromethyl)-5-(4-iodophenyl)-2,2-dimethyloxazolidine-3-carboxylate (2.0 g, 4.6 mmols) is added ethynyltrimethylsilane (451 mg, 4.6 mmols), copper (I)iodide (88 mg, 0.46 mmols, 0.1 equivs), Bis(triphenylphosphine)palladium(II)dichloride (165 mg, 0.23 mmols, 0.05 equivs) and piperidine (782 mg, 9.2 mmols, 2 equivs). The mixture is heated in an atmosphere of nitrogen at 35° C. for six hours. The mixture is filtered through a pad of Celite. The pad of Celite is washed with ethylacetate (2×15 ml). The combined organic filtrates were concentrated using rotary evaporation at reduced pressure to give a crude viscous oil. The oil is purified by flash column chromatography (grading from 100% hexanes to 15% EtOAc) to give the title compound (1.65 g): m/z (Cl) 306 ([M+H]+-Boc).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09073894B2 |
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| Source dataset | uspto-grants-2015_07 |
|---|
| ORD ID | ord-2fb93e4e686c410a85c66d7247d3d269 |
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| Source note | uspto-grants-2015_07 |
|---|
