HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → Cyclopropyl-methyl-(4-methyl-3-trimethylsilanylethynyl-benzyl)-amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Trimethylsilylacetylene | HCID 66111 | — |
| Reactant | Benzenemethanamine, 3-bromo-N-cyclopropyl-N,4-dimethyl- | HCID 21107149 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Cyclopropyl-methyl-(4-methyl-3-trimethylsilanylethynyl-benzyl)-amine | HCID 57424248 | 94.1% |
Reaction Steps
Following General Procedure D and using cyclopropyl-(3-bromo-4-methyl-benzyl)-methyl-amine (Intermediate 97, 2.24 g, 8.81 mmol), triethyl amine (10 mL), tetrahydrofuran (5 mL), copper(I)iodide (0.4 g, 2.1 mmol), trimethylsilyl acetylene (5 mL, 35.4 mmol) and dichlorobis(triphenylphosphine)palladium(II) (1.45 g, 2.06 mmol) followed by flash column chromatography over silica gel (230–400 mesh) using 6–10% ethyl acetate in hexane as the eluent, the title compound (2.25 g, 94%) was obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07226951B2 |
| Source dataset | uspto-grants-2007_06 |
| ORD ID | ord-777d5f67cb6e48649a6b76f2686969e6 |
| Source note | uspto-grants-2007_06 |