Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | HCID 66585051 | HCID 66585051 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 66585108 | HCID 66585108 | 92.5% |
Reaction Steps
To a suspension of 1.24 g (3.00 mmol) of 2-tert-butyl 8-ethyl 6-cyano-7-(3-fluorophenyl)-3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1H)-dicarboxylate in 15 ml of a mixture of ethanol, water and tetrahydrofuran (1:1:1) is added 0.086 g (3.6 mmol) of lithium hydroxide, and the mixture is heated at 60° C. for 1 day. The mixture is then taken up in 60 ml of dichloromethane and is acidified by addition of aqueous 1N sulfuric acid. The organic phase is separated out and dried over sodium sulfate, and the solvent is evaporated off under reduced pressure to give a solid, which is triturated in acetonitrile to give 1.07 g of 2-(tert-butyloxycarbonyl)-6-cyano-7-(3-fluorophenyl)-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-8-carboxylic acid in the form of a white powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09233965B2 |
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| Source dataset | uspto-grants-2016_01 |
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| ORD ID | ord-b2d52366d77648a88d2af9d8c3dc6dc4 |
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| Source note | uspto-grants-2016_01 |
|---|