Water → [(2R,6S)-6-(4-chlorophenyl)piperidin-2-yl]methanol
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C@H:14]2[NH:19][C@@H:18]([C:20](OC)=[O:21])[CH2:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1.O.[OH-].[Na+]>C1COCC1.C(OCC)(=O)C>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C@H:14]2[NH:19][C@@H:18]([CH2:20][OH:21])[CH2:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -20 °C
Procedure
Lithium aluminum hydride (508 mg) was suspended in THF (50 mL) in a nitrogen atmosphere. Methyl (2R,6S)-6-(4-chlorophenyl)piperidine-2-carboxylate (2.47 g) was added to the suspension at −20° C., and the reaction solution was stirred at −20° C. for one hour. Water (0.51 ml), a 5 N sodium hydroxide solution (0.51 ml), and water (1.53 ml) were sequentially added to the reaction solution at −20° C., and the reaction solution was stirred at room temperature for 15 minutes. Ethyl acetate was added to the reaction solution. Then, the reaction solution was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system) to obtain 1.90 g of the title compound. The property value of the compound is as follows.
Workup
- stirringthe reaction solution was stirred at room temperature for 15 minutes
- filtrationThen, the reaction solution was filtered through celite
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (carrier: Chromatorex NH; elution solvent: heptane-ethyl acetate system)
Sources & evidence
- ORD record
- ord-3cdcfb92dc344b60b25eb750a4f762c8
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07618960B2
Reaction notes
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