Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | alpha-Cyclopentylmandelic acid | HCID 98283 | — |
| Reactant | (3S)-(+)-1-Benzyl-3-aminopyrrolidine | HCID 1519353 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 9999727 | HCID 9999727 | 95% |
Reaction Steps
The compound 2-cyclopentyl-2-hydroxy-2-phenylacetic acid (0.52 g, 2.36 mM) and (3S)-1-benzyl-3-aminopyrrolidine (0.5 g, 2.84 mM) were dissolved in dimethylformamide (10.0 ml) and N-methylmorpholine (1.3 ml, 11.8 mM) was added into it followed by the addition of 1-hydroxybenzotriazole (0.32 g, 2.36 mM) at 0-5° C. The reaction mixture was maintained at 0-5° C. for 1 hour and then at room temperature for 19 hours. The reaction mixture was poured into water (100.0 ml) with constant stirring. The organic compound was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated sodium bicarbonate water and brine solution followed its drying and concentration over anhydrous sodium sulphate. The residue was purified by silica gel column chromatography using 10% methanol in chloroform to get the title compound. Yield=95% (0.5 g, 2.38 mM).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07465751B2 |
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| Source dataset | uspto-grants-2008_12 |
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| ORD ID | ord-71cf3078921e45ce96d1fc6b77b826c3 |
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| Source note | uspto-grants-2008_12 |
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