Methanol → 1,3-Piperidinedicarboxylic acid, 5-methyl-, 1-(1,1-dimethylethyl) ester
Reaction equation
[CH3:1][CH:2]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5][CH:4]([C:15]([O:17]C)=[O:16])[CH2:3]1.O1CCOCC1.CO.[OH-].[Na+]>O>[C:11]([O:10][C:8]([N:6]1[CH2:7][CH:2]([CH3:1])[CH2:3][CH:4]([C:15]([OH:17])=[O:16])[CH2:5]1)=[O:9])([CH3:12])([CH3:13])[CH3:14]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
136B was dissolved with dioxane (14 mL) and methanol (7 mL). Sodium hydroxide (1.32 g, 33 mmol) in water (2 mL) was added and the mixture was heated to 80° C. for 5 hrs. Solvent was removed under vacuum and the residue was partitioned between 2N HCl (50 mL) and ethyl acetate (50 mL). The mixture was transferred to a separatory funnel and the organics were separated. The aqueous layer was extracted with ethyl acetate (2×25 mL), and the organics were combined and dried over sodium sulfate and filtered. Solvent was removed under vacuum to leave 1-(tert-butoxycarbonyl)-5-methylpiperidine-3-carboxylic acid (136C) as a white solid which was used without further purification. ESI-MS:m/z 266.4 (M+H)+.
Workup
- customSolvent was removed under vacuum
- customthe residue was partitioned between 2N HCl (50 mL) and ethyl acetate (50 mL)
- customThe mixture was transferred to a separatory funnel
- customthe organics were separated
- extractionThe aqueous layer was extracted with ethyl acetate (2×25 mL)
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customSolvent was removed under vacuum
Sources & evidence
- ORD record
- ord-93c83d680e1f4edb9a388565678b9de0
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08138168B1
Reaction notes
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