Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Picolinic acid | HCID 1018 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 2,3-Dimethyliodobenzene | HCID 141645 | — |
| Reactant | 2-(4-Hydroxy-phenyl)-morpholine-4-carboxylic acid tert-butyl ester | HCID 66654239 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Sodium chloride; water | HCID 57417360 | — |
| Product | HCID 66653709 | HCID 66653709 | — |
Reaction Steps
To a degassed solution of 2-(4-hydroxy-phenyl)-morpholine-4-carboxylic acid tert-butyl ester (10.23 g; 36.6 mmol), and 1-iodo-2,3-dimethyl-benzene (10.62 g; 45.8 mmol) in DMSO (50 mL), was added picolinic acid (0.90 g; 7.3 mmol), CuI (0.70 g; 3.7 mmol) and K3PO4 (15.55 g; 73.3 mmol). The resulting mixture was heated overnight, at 90° C. After cooling to RT, brine was added and the mixture extracted with CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, CH2Cl2) to afford 2-[4-(2,3-dimethyl-phenoxy)-phenyl]-morpholine-4-carboxylic acid tert-butyl ester.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09029371B2 |
|---|
| Source dataset | uspto-grants-2015_05 |
|---|
| ORD ID | ord-d646cfaf2d234009a22bae0a8e0e0f5d |
|---|
| Source note | uspto-grants-2015_05 |
|---|
