Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | HCID 117778625 | HCID 117778625 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Menthol | HCID 1254 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 89740157 | HCID 89740157 | 94.2% |
Reaction Steps
To a solution of sodium hydroxide solution (50 mg, 1.2 mmol) in tetrahydrofuran, menthol and water (20 mL, 3:1:1, V/V) was added methyl 2-methyl-1-(1-oxo-1-(pyrrolidin-1-yl)propan-2-yl)-1H-indole-3-carboxylate (100 mg, 0.318 mmol). The reaction mixture was stirred at 70° C. for 10 hours. The mixture was quench with 10% hydrochloric acid aqueous (2 mL), extracted with dichloromethane and menthol (60 mL, 10:1). The combine organic layer was dried by anhydrous sodium sulfate, filtered and concentrated to give 2-methyl-1-(1-oxo-1-(pyrrolidin-1-yl)propan-2-yl)-1H-indole-3-carboxylic acid (90 mg, 92%). LCMS (M+H+) m/z: calcd 300.15. found 300.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09371331B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-5479a7d1794b4789a84aea0c30763c68 |
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| Source note | uspto-grants-2016_06 |
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