Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethylene Glycol | HCID 174 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 4-Bromo-2-chloro-1-iodobenzene | HCID 2735547 | — |
| Reactant | HCID 178455327 | HCID 178455327 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | 1-Butanol | HCID 263 | — |
| Product | HCID 178455329 | HCID 178455329 | — |
Reaction Steps
A mixture of (5S)-2-(cis-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-2,7-diazaspiro[4.5]decan-1-one (0.282 g, 0.000769 mol), 4-bromo-2-chloro-1-iodobenzene (0.293 g, 0.000922 mol) (Lancaster, cat #: 19245), copper(I) iodide (0.015 g, 0.000077 mol), potassium phosphate (0.490 g, 0.00231 mol) and 1,2-ethanediol (0.0857 mL, 0.00154 mol) in 1-butanol (0.75 mL) was heated at 100° C. under nitrogen for 2 d. The reaction mixture was filtered, concentrated under reduced pressure, and the residue was purified by flash chromatography on a silica gel column (eluting with 0 to 50% ethyl acetate in hexanes) to afford the desired product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09371323B2 |
|---|
| Source dataset | uspto-grants-2016_06 |
|---|
| ORD ID | ord-d65a674e4a2b4f05af291e7a66df27a4 |
|---|
| Source note | uspto-grants-2016_06 |
|---|
