Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | HCID 77858697 | HCID 77858697 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 68427102 | HCID 68427102 | 106% |
Reaction Steps
In a nitrogen atmosphere, 152 mg of lithiumaluminium hydride was added to tetrahydrofuran (20 mL) solution of 500 mg of methyl (3RS,4SR)-1-methyl-4-o-tolylpiperidine-3-carboxylate obtained in Production Example 31-1, at 0° C., and stirred at 0° C. for 30 minutes. 0.15 mL of water, 0.15 mL of aqueous 15% sodium hydroxide solution and 0.46 mL of water were added to the reaction liquid in that order, and stirred at room temperature for 1 hour. This was diluted with ethyl acetate, and dried with anhydrous sodium sulfate, and the insoluble substance was removed through filtration through Celite. The filtrate was distilled under reduced pressure, and the residue was separated and purified through silica gel column chromatography (chloroform/methanol=70/30) to obtain 470 mg of the entitled compound as a pale yellow oily substance.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07855294B2 |
|---|
| Source dataset | uspto-grants-2010_12 |
|---|
| ORD ID | ord-f93b1d069eb944e1b3ee937f5e822f9f |
|---|
| Source note | uspto-grants-2010_12 |
|---|