Sodium Hydroxide → 1-((Tert-butoxy)carbonyl)-5-(methoxycarbonyl)piperidine-3-carboxylic acid
Reaction equation
[N:1]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:6][CH:5]([C:7]([O:9]C)=[O:8])[CH2:4][CH:3]([C:11]([O:13][CH3:14])=[O:12])[CH2:2]1.[OH-].[Na+]>CO>[C:18]([O:17][C:15]([N:1]1[CH2:2][CH:3]([C:11]([O:13][CH3:14])=[O:12])[CH2:4][CH:5]([C:7]([OH:9])=[O:8])[CH2:6]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]Participants
4
Procedure
1-tert-Butyl 3,5-dimethyl piperidine-1,3,5-tricarboxylate (75 g) was dissolved in methanol (375 ml), and 2 M aqueous sodium hydroxide solution (125 ml) was added dropwise at room temperature. The reaction mixture was stirred at room temperature for 14 hr, and methanol was evaporated under reduced pressure. The concentrated solution was diluted with saturated aqueous sodium hydrogen carbonate solution (100 ml) and washed twice with ethyl acetate. The basic aqueous layer was acidified (pH 2) with 6 M hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the object compound (71 g).
Workup
- custommethanol was evaporated under reduced pressure
- additionThe concentrated solution was diluted with saturated aqueous sodium hydrogen carbonate solution (100 ml)
- washwashed twice with ethyl acetate
- extractionthe mixture was extracted with ethyl acetate
- dry with materialThe extract was dried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-8a7ee7d380644e59bedb01b4e87e48fd
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08329691B2
Reaction notes
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