Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | N-Fluorobenzenesulfonimide | HCID 588007 | — |
| Reactant | (R)-4-[6-(4-tert-Butylcyclohexyloxy)naphthalen-2-yl]-4-methyl-oxazolidin-2-one | HCID 67414115 | — |
| Catalyst | Zirconium chloride (ZrCl4), (T-4)- | HCID 9856075 | — |
| Product | HCID 178445736 | HCID 178445736 | 42% |
Reaction Steps
(R)-4-[6-(4-tert-Butyl-cyclohexyloxy)-naphthalen-2-yl]-4-methyl-oxazolidin-2-one (0.3012 g, 0.0007895 mol) was dissolved in methylene chloride (5.00 mL, 0.0780 mol) in a capped 40 mL vial equipped with a magnetic stir bar. N-fluoro-N-(phenylsulfonyl)benzenesulfonamide (0.249 g, 0.000789 mol) was added followed by zirconium tetrachloride (0.184 g, 0.000789 mol) and the mixture was heated overnight at 40° C. The reaction mixture was cooled to room temperature then concentrated to dryness under reduced pressure, adsorbed onto silica gel and purified by flash chromatography (0-55% EtOAc in hexanes) to give 131.3 mg of the title compound (42% yield).
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-f698c23f4a2947fbb83c69a07156e9e5 |
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| Source note | uspto-grants-2013_10 |
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