Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Boron tribromide | HCID 25134 | — |
| Reactant | HCID 45480480 | HCID 45480480 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 59486028 | HCID 59486028 | 88.2% |
Reaction Steps
A solution of (S)-1-(4-(4-chlorophenoxy)phenyl)-5-(3-methoxyphenyl)-imidazolidin-2-one (99 mg, 0.25 mmol) in CH2Cl2 (2 mL) is cooled to −78° C. when BBr3 (1 mmol, 1 mL of 1M solution in CH2Cl2) is added drop wise. After the addition, the mixture is warmed to 0° C. and stirred for 1 h when MeOH (0.5 mL) is added into the mixture to quench the reaction. The reaction mixture is then treated with water (3 mL) and extracted with EtOAc (3×5 mL). The combined organic layers are concentrated and purified by flash column chromatography (silica gel, 0-100% EtOAc/hexane) to provide the titled compound as a white solid (84 mg, 88%). HPLC-MS calculated for C21H17ClN2O3 (M+H+) 381.1, found 381.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08431607B2 |
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| Source dataset | uspto-grants-2013_04 |
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| ORD ID | ord-a0d595a5a6ad4d59a8917d13db87a143 |
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| Source note | uspto-grants-2013_04 |
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