Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | HCID 131734657 | HCID 131734657 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 131734656 | HCID 131734656 | — |
Reaction Steps
To a solution of (3R)-ethyl 5bromo-3-methylisochroman-1-carboxylate (2.0 g, 5.95 mmol) in dioxane (50 ml) and water (10 ml) was added KOH (1.37 g, 35.7 mmol), tetramethyl dit-butyl XPhos (0.28 g, 0.06 mmol) and Pd2(dba)3 (0.06 g, 0.06 mmol) at room temperature. Then, reaction mixture was degassed three times with N2 and stirred at 100° C. for 16 h. The reaction mixture was quenched with MeOH and concentrated under reduced pressure to afford crude compound. The crude was dissolved in EtOH (80 ml) added H2SO4 (1.0 ml) then stirred at 80° C. for 5 h. The solvent was removed by evaporation to get the crude compound. The title compound was purified by separation methods A and E. (Yield 100 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09249127B2 |
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| Source dataset | uspto-grants-2016_02 |
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| ORD ID | ord-b564badd37f24870b59340c04e7db103 |
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| Source note | uspto-grants-2016_02 |
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