Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Heptane | HCID 8900 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Lithium Chloride | HCID 433294 | — |
| Reactant | HCID 67033070 | HCID 67033070 | — |
| Reactant | HCID 178418750 | HCID 178418750 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67032694 | HCID 67032694 | — |
Reaction Steps
3-{2-[4-(2,6-Dichloro-4-iodo-benzyloxy)-phenyl]-morpholin-4-yl}-propionic acid tert-butyl ester (0.34 g; 0.57 mmol), and Pd(dppf)Cl2 (14.70 mg; 0.02 mmol) were added to a solution of lithium chloride (4.59 ml; 0.50 mol/l; 2.30 mmol) in THF; 0.04 eq.). The resulting mixture was cooled to 0° C. and a solution of diethylzinc in n-heptane (1.15 ml; 1.00 mol/l; 1.15 mmol) was added dropwise. The mixture was heated to 60° C. overnight. After cooling to RT saturated aqueous NH4Cl was added. The mixture was extracted with EtOAc. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, EtOAc:hexanes 1:1) to afford 3-{2-[4-(2,6-dichloro-4-ethyl-benzyloxy)-phenyl]-morpholin-4-yl}-propionic acid tert-butyl ester (115.00 mg)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09045441B2 |
|---|
| Source dataset | uspto-grants-2015_06 |
|---|
| ORD ID | ord-8081e0c4fb5d409aaf01b83e152ef28e |
|---|
| Source note | uspto-grants-2015_06 |
|---|
