Lithium Hydroxide → 1-[(Benzyloxy)carbonyl]-3-methylpiperidine-3-carboxylic acid
Reaction equation
[CH3:1][C:2]1([C:18]([O:20]CC)=[O:19])[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:3]1.[Li+].[OH-]>C(O)C>[CH2:11]([O:10][C:8]([N:4]1[CH2:5][CH2:6][CH2:7][C:2]([CH3:1])([C:18]([OH:20])=[O:19])[CH2:3]1)=[O:9])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 86 °C
Procedure
To 1-benzyl 3-ethyl 3-methylpiperidine-1,3-dicarboxylate (3.0 g, 10.0 mmol) in ethanol (15 mL) was added LiOH (15.0 mL, 30.1 mmol), and the reaction mixture was stirred at 86° C. for 1 hour. The ethanol was removed, and ether (30 mL) was added. The aqueous layer was separated and acidified with saturated potassium hydrogen sulfate to a pH of about 3 to about 4, extracted with ethyl acetate (50 mL), and washed with brine and dried over sodium sulfate. After removal of the solvent, 1-(benzyloxycarbonyl)-3-methylpiperidine-3-carboxylic acid (2.6 g, 92% yield) was isolated as an oil.
Workup
- customThe ethanol was removed
- additionether (30 mL) was added
- customThe aqueous layer was separated
- extractionextracted with ethyl acetate (50 mL)
- washwashed with brine
- dry with materialdried over sodium sulfate
- customAfter removal of the solvent
Sources & evidence
- ORD record
- ord-68221727929649b6855ef87081d2f5d2
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08545897B2
Reaction notes
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