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 2M 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 concentrate 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 6M 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 product (71 g).
Workup
- custommethanol was evaporated under reduced pressure
- additionThe concentrate 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-3a774e58a7f045cb9a18946b1d281216
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09045436B2
Reaction notes
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