Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzyl Alcohol | HCID 244 | — |
| Reactant | 1,10-Phenanthroline | HCID 1318 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | HCID 66654135 | HCID 66654135 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67032998 | HCID 67032998 | 88.1% |
Reaction Steps
(All solutions were degassed) To a suspension of 1,10-phenanthroline (183.0 mg; 1.02 mmol) in toluene (15 mL) was added CuI (96.7 mg; 0.51 mmol), Cs2CO3 (3.31 g; 10.15 mmol), and a solution of 3-[2-(4-iodo-phenyl)-thiomorpholin-4-yl]-propionic acid tert-butyl ester (2.20 g; 5.08 mmol) and benzyl alcohol (1.05 mL; 10.15 mmol) in toluene (20 mL). The resulting mixture was heated for three days at 100° C. After cooling to RT EtOAc and water were added. The layers were separated and the organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, EtOAc/CH2Cl2 1:6) to afford 3-[2-(4-benzyloxy-phenyl)-thiomorpholin-4-yl]-propionic acid tert-butyl ester (1.85 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09273017B2 |
|---|
| Source dataset | uspto-grants-2016_03 |
|---|
| ORD ID | ord-fd6e09078e0f43c49dd808889c61f3d8 |
|---|
| Source note | uspto-grants-2016_03 |
|---|
