HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diethylamine → 2-(4-{8-[(Cyclopropyl-methyl-amino)-methyl]-2,2,4,4-tetramethyl-chroman-6-ylethynyl}-phenyl)-2-methyl-propionic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diethylamine | HCID 8021 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 8-[(Cyclopropyl-methyl-amino)methyl]-6-ethynyl-2,2,4,4-tetramethyl-chroman | HCID 21107250 | — |
| Reactant | 2-{4-[(8-Cyclopropyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl)ethynyl]-phenyl}-2-methyl-propionic acid methyl ester | HCID 69077341 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | 2-(4-{8-[(Cyclopropyl-methyl-amino)-methyl]-2,2,4,4-tetramethyl-chroman-6-ylethynyl}-phenyl)-2-methyl-propionic acid methyl ester | HCID 69074187 | — |
Reaction Steps
Following General Procedure B and using 8-[(cyclopropyl-methyl-amino)-methyl]-6-ethynyl-2,2,4,4-tetramethyl-chroman (Intermediate 11, 0.08 g, 0.27 mol), methyl-2-(4-iodophenyl)-2-methyl-propionate (Reagent 2, 0.082 g, 0.27 mol), diethyl amine (2 mol), copper(I)iodide (0.020 g, 0.1 mol) and dichlorobis(triphenylphosphine)palladium(II) (0.07 g, 0.1 mol) followed by flash column chromatography over silica gel (230-400 mesh) using 10% ethyl acetate in hexane as the eluent, the title compound was obtained as a brown oil (0.040 g, 31%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07468391B2 |
| Source dataset | uspto-grants-2008_12 |
| ORD ID | ord-155b4b9035c34165aa21d1f8a7b7c076 |
| Source note | uspto-grants-2008_12 |