Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Diisobutylaluminum hydride | HCID 14487 | — |
| Reactant | (4-{4-[2-(3-Chlorophenylamino)-oxazol-5-yl]-phenyl}-cyclohexyl)-acetic acid ethyl ester | HCID 66615762 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Potassium Sodium Tartrate | HCID 9357 | — |
| Product | HCID 86634689 | HCID 86634689 | 56.2% |
Reaction Steps
To a solution of (4-{4-[2-(3-Chlorophenylamino)-oxazol-5-yl]-phenyl}-cyclohexyl)-acetic acid ethyl ester (500 mg, 1.14 mmol) in DCM (20 mL) at −78° C. is added DIBAL-H (1 M in toluene, 2.14 mL, 2.14 mmol) and the mixture is allowed to stir at −78° C. for 2 h. Methanol (3 mL) is added to quench the reaction. The reaction mixture is then poured in ice and Rochelle's salt (4 g). Water (20 mL) is added and the mixture is extracted with EtOAc (3×30 mL). The organic phase is washed with brine (3×30 mL), dried with Na2SO4 and concentrated to give the title compound (253 mg) as a white solid: (M+H)+395.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08835451B2 |
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| Source dataset | uspto-grants-2014_09 |
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| ORD ID | ord-4b7103a215f94e4db1935e71a1e98126 |
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| Source note | uspto-grants-2014_09 |
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