HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 30763Generated: October 29, 2026
Ethyl Acetate → 4-((1R,2S)-2-(2-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethylamino}-1-hydroxypropyl)phenol
https://huagongshe.com/reaction/30763
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | P-Hydroxynorephedrine | HCID 6931143 | — |
| Reactant | Ethanol, 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]-, 1-methanesulfonate | HCID 86605506 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-((1R,2S)-2-(2-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethylamino}-1-hydroxypropyl)phenol | HCID 68545025 | 16.6% |
Reaction Steps
A mixture of 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethyl methanesulfonate (1.20 g) and 4-((1R,2S)-2-amino-1-hydroxypropyl)phenol (1.76 g) in N,N-dimethylformamide (20 mL) was stirred at 80° C. for 5 hrs. Ethyl acetate was added to the reaction mixture. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent:n-hexane/ethyl acetate=1/1, methylene chloride/methanol=9/1) to afford the title compound (0.24 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07423185B2 |
|---|
| Source dataset | uspto-grants-2008_09 |
|---|
| ORD ID | ord-8c7618feeee049eebb73358fc74bc42e |
|---|
| Source note | uspto-grants-2008_09 |
|---|