Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Lithium Chloride | HCID 433294 | — |
| Reactant | Ethylacetate methanol | HCID 21584119 | — |
| Reactant | 5-(1H-Indole-3-carbonyloxy)-10-oxo-8-aza-tricyclo[5.3.1.03,8]undecane-9-carboxylic acid methyl ester | HCID 57693709 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Anzemet | HCID 3148 | 83% |
Reaction Steps
A mixture of 3.1 gr (8.1 mmol) of 5-(1H-Indole-3-carbonyloxy)-10-oxo-8-aza-tricyclo[5.3.1.03,8]undecane-9-carboxylic acid methyl ester and LiCl (0.69 gr, 16.23 mmol) in dimethylformamide (90 mL) is heated to 140° C. Once 4 hours have elapsed, and after checking by thin-layer chromatography (AcOEt/MeOH 9:1) that the reaction has been completed, the mixture is left to cool. Volatile substances are evaporated at low pressure and the residue is dissolved in dichloromethane (150 mL). This is washed with a saturated aqueous solution of NaCl (70 mL), and the organic phase is dried over magnesium sulphate and evaporated, to provide crude 1H-Indole-3-carboxylic acid 10-oxo-8-aza-tricyclo[5.3.1.03,8]undec-5-yl ester as a solid (2.18 gr, 83%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07745628B2 |
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| Source dataset | uspto-grants-2010_06 |
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| ORD ID | ord-889f3a8880784feb9fedf8b812d840f5 |
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| Source note | uspto-grants-2010_06 |
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