Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethylmorpholine | HCID 7525 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | 4-Carbomethoxy-2-methylbutanoic acid | HCID 13192897 | — |
| Reactant | Methyl 2-azabicyclo[2.2.1]heptane-3-carboxylate hydrochloride | HCID 20487957 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 20487949 | HCID 20487949 | 57.4% |
Reaction Steps
A mixture of 3.83 g (0.02 m) of 3-carbomethoxy-2-azabicyclo[2.2.1]heptane hydrochloride from Example 1, 3.29 g (0.02 m) of 4-carbomethoxy-2-methylbutanoic acid, 2.3 g of N-ethylmorpholine, 5.4 g of 1-hydroxybenzotriazole, 4.13 g of dicyclohexylcarbodiimide and 60 ml of dry tetrahydrofuran was prepared with cooling and stirring, then, allowed to stir at room temperature for 18 hours. The mixture was filtered. The filtrate was evaporated to give a syrup which was dissolved in ethyl acetate and washed with 10% acetic acid/water and water. A solid separated. The ethyl acetate extract was further washed with 5% sodium bicarbonate solution and brine, then, dried and evaporated under reduced pressure to give 3.41 g (57%) of 3-carbomethoxy-2-(4-carbomethoxy-2-methylbutanoyl)-2-azabicyclo[2.2.1]heptane, mE 297.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04405787 |
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| Source dataset | uspto-grants-1983_09 |
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| ORD ID | ord-83a1bb81f19b4c309f8086510a1c8229 |
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| Source note | uspto-grants-1983_09 |
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