Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Isopropoxybenzeneboronic acid | HCID 3698726 | — |
| Reactant | (R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one | HCID 51066623 | — |
| Product | HCID 67414948 | HCID 67414948 | 63.6% |
Reaction Steps
(R)-4-(6-hydroxynaphthalen-2-yl)-4-methyloxazolidin-2-one (3 g, 0.01 mol), 4-isopropoxyphenylboronic acid (5 g, 0.03 mol), and cupric acetate (2.55 g, 0.0140 mol) were placed in a vial followed by methylene chloride (100 mL, 2 mol) and finally triethylamine (9.78 mL, 0.0702 mol) at 23° C. The flask was then purged with nitrogen, sealed and stirred at room temperature overnight. The reaction was allowed to stir for 16 hours. Reaction was then heated to 50° C. for two hours. The reaction mixture was then cooled to RT and filtrated and the crude material was then purified via chromatography (SiO2, 40 g, 0-75% EtOAC/Hexane) to give 2.4 g of the desired product as a colorless solid. Material was used without additional purification. ESI-MS: 378 (M+H)+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08546359B2 |
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| Source dataset | uspto-grants-2013_10 |
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| ORD ID | ord-4d6ce0ecc54744e29d0fc6b386e04263 |
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| Source note | uspto-grants-2013_10 |
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