HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl propiolate → HCID 178498825, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl propiolate | HCID 13536 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 178418853 | HCID 178418853 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 178498825 | HCID 178498825 | 65% |
Reaction Steps
To a THF (30 ml) solution under Ar of (cis-4-azido-cyclohexyl)carbamic acid tert-butyl ester (3.00 g) and propiolic acid methyl ester (1.05 g) were added CuI (2.38 g) and DIPEA (3.18 ml). The resulting slurry was stirred at RT over night. After dilution with EtOAc (200 ml) the mixture was washed with H2O (200 ml), dried over Na2SO4 and the solvent was evaporated. Chromatography (silica, CH2Cl2/MeOH 95:5) yielded 2.63 g (65%) of product. White crystals. MS 325.4 (95, [M+H]+), 269.4 (100, [M−tBu].+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07268154B2 |
| Source dataset | uspto-grants-2007_09 |
| ORD ID | ord-70ca05cbca7c4c4fa94de4cb82dac050 |
| Source note | uspto-grants-2007_09 |