HuagongsheHuagongshe Chemistry Print Report · For research reference only
[5-{(1R)-2-[(2-{4-[2-(1-adamantyl)ethoxy]phenyl}ethyl)-amino]-1-hydroxyethyl}-2-(benzyloxy)phenyl]formamide → (5-{(1R)-2-[(2-{4-[2-(1-adamantyl)ethoxy]phenyl}ethyl)amino]-1-hydroxyethyl}-2-hydroxyphenyl)formamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | [5-{(1R)-2-[(2-{4-[2-(1-adamantyl)ethoxy]phenyl}ethyl)-amino]-1-hydroxyethyl}-2-(benzyloxy)phenyl]formamide | HCID 86649159 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (5-{(1R)-2-[(2-{4-[2-(1-adamantyl)ethoxy]phenyl}ethyl)amino]-1-hydroxyethyl}-2-hydroxyphenyl)formamide | HCID 59624929 | 38.1% |
Reaction Steps
To a solution of Intermediate 26 (0.32 g, 0.56 mmol) in a mixture of methanol (5 mL) and tetrahydrofuran (5 mL) was added palladium on charcoal (10%, 0.03 g). The reaction mixture was hydrogenated at 40 psi for 3 days. The catalyst was filtered through Celite® and the solvent removed under reduced pressure. The crude was purified by chromatography eluting with chloroform/methanol (6:1) to give the title compound as a solid (0.102 g, 37%)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08178679B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-a6becfff89394e6eaed903e779273a83 |
| Source note | uspto-grants-2012_05 |