Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | methyl (2R,6S)-6-(3,4,5-trifluorophenyl)piperidine-2-carboxylate | HCID 67372196 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67371748 | HCID 67371748 | 98.4% |
Reaction Steps
Under a nitrogen atmosphere, a tetrahydrofuran (10 mL) solution of (2R,6S)-6-(3,4,5-trifluorophenyl)piperidine-2-carboxylic acid methyl ester (3.25 g) was added dropwise at −20° C. into a tetrahydrofuran (50 mL) suspension of lithium aluminum hydride (621 mg). After confirming the disappearance of the raw materials, water (0.62 mL), 5 N sodium hydroxide solution (0.62 mL), and water (1.86 mL) were added in sequence to the reaction solution at the same temperature. After stirring for 15 minutes at the same temperature, ethyl acetate was added, and the resultant was filtered on celite. The filtrate was passed through a silica pad (carrier: Chromatrex NH, eluting solvent: ethyl acetate), and by removing the solvent under a vacuum, the title compound (2.87 g) was obtained. The physical property values are as follows.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08008293B2 |
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| Source dataset | uspto-grants-2011_08 |
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| ORD ID | ord-cc05be737a0148189c265a275420dbea |
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| Source note | uspto-grants-2011_08 |
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