Lithium hydroxide, monohydrate → 1-(tert-Butoxycarbonyl)-4-((tert-butoxycarbonyl)amino)piperidine-4-carboxylic acid
Reaction equation
O.[OH-].[Li+].[C:4]([O:8][C:9]([NH:11][C:12]1([C:25]([O:27]C)=[O:26])[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]>O.C1COCC1.CO.CCOC(C)=O>[C:21]([O:20][C:18]([N:15]1[CH2:14][CH2:13][C:12]([NH:11][C:9]([O:8][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:10])([C:25]([OH:27])=[O:26])[CH2:17][CH2:16]1)=[O:19])([CH3:24])([CH3:23])[CH3:22]Participants
7
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 20 °C
Procedure
Lithium hydroxide monohydrate (8.13 g, 193.62 mmol) was added to 1-tert-butyl 4-methyl 4-(tert-butoxycarbonylamino)piperidine-1,4-dicarboxylate (Intermediate 69) (13.88 g, 38.72 mmol) in water (21.51 mL), THF (86 mL) and methanol (86 mL). The resulting solution was stirred at 20° C. for 1 day. The reaction mixture was diluted with EtOAc (75 mL) and washed with water (75 mL). The aqueous was adjusted to pH5 with 1M citric acid solution, then extracted with EtOAc (3×200 mL). The organic extracts were washed with saturated brine (50 mL), then dried over MgSO4, filtered and evaporated to afford desired product 1-(tert-butoxycarbonyl)-4-(tert-butoxycarbonylamino)piperidine-4-carboxylic acid (10.36 g, 78%) as a fine white solid.
Workup
- washwashed with water (75 mL)
- extractionextracted with EtOAc (3×200 mL)
- washThe organic extracts were washed with saturated brine (50 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-0232f0a19c67453e81abacbe2e78a0b4
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08101623B2
Reaction notes
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