Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diisopropylamine | HCID 7912 | — |
| Reactant | P-Hydroxynorephedrine | HCID 6931143 | — |
| Reactant | Ethyl 4'-(2-methanesulfonyloxyethoxy)biphenyl-4-carboxylate | HCID 23090736 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 68540484 | HCID 68540484 | 57.5% |
Reaction Steps
Diisopropylamine (0.40 mL) was added to a mixture of ethyl 4′-(2-methanesulfonyloxyethoxy)biphenyl-4-carboxylate (0.32 g) and 4-((1R,2S)-2-amino-1-hydroxypropyl)phenol (0.32 g) in N,N-dimethylformamide (6 mL), and the mixture was stirred for 14 hrs at 80° C. After being cooled to room temperature, the reaction mixture was partitioned between methylene chloride and water. 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: methylene chloride/methanol=15/1) to afford ethyl 4′-{2-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl-amino]ethoxy}biphenyl-4-carboxylate (0.22 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07674938B2 |
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| Source dataset | uspto-grants-2010_03 |
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| ORD ID | ord-c5d4a28785924b7284739943c0859d33 |
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| Source note | uspto-grants-2010_03 |
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