HuagongsheHuagongshe Chemistry Print Report · For research reference only
Diisopropylethylamine → Tert-Butyl (1S,3S,4S,5S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | 1-Hydroxybenzotriazole hydrate | HCID 2796029 | — |
| Reactant | (2S)-Pyrrolidine-2-carbonitrile hydrochloride | HCID 44593801 | — |
| Reactant | (1S,3S,4S,5S,6R)-2-(tert-Butoxycarbonyl)-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-3-carboxylic Acid | HCID 69134634 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Tert-Butyl (1S,3S,4S,5S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-2-carboxylate | HCID 86598887 | — |
Reaction Steps
To a solution of (1S,3S,4S,5S,6R)-2-(tert-butoxycarbonyl)-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-3-carboxylic acid obtained in Example 1-3 (500 mg) 1-hydroxybenzotriazole hydrate (415 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (493 mg) in dimethylformamide (10 mL), were added diisopropylethylamine and (2S)-2-pyrrolidinecarbonitrile hydrochloride with cooling on an ice bath. The reaction mixture was stirred at that temperature for 3 hrs.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07186731B2 |
| Source dataset | uspto-grants-2007_03 |
| ORD ID | ord-f4a85ca8b372443c83aae2e22ba635fc |
| Source note | uspto-grants-2007_03 |