Ethanol → (R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidinecarboxylic acid
Reaction equation
[Li+].[OH-].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13](/[CH:16]=[CH:17]/[C:18]([N:20]2[CH2:25][CH2:24][CH2:23][C@@H:22]([C:26]([O:28]CC)=[O:27])[CH2:21]2)=[O:19])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].CCO>O.O1CCCC1>[C:3]([O:7][C:8]([N:10]1[CH2:11][CH2:12][CH:13](/[CH:16]=[CH:17]/[C:18]([N:20]2[CH2:25][CH2:24][CH2:23][C@@H:22]([C:26]([OH:28])=[O:27])[CH2:21]2)=[O:19])[CH2:14][CH2:15]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of LiOH (0.32 g) in H2O (20 ml) was added to a solution of ethyl (R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidinecarboxylate (4.46 g) in tetrahydrofuran (20 ml)-EtOH (20 ml) at 0° C. The reaction mixture was stirred for 3 hours at the same condition, and the solvent was evaporated in vacuo. The residue was resolved in ethyl acetate-water, and acidified with 10% aq. KHSO4. The whole was washed with water, brine, dried over MgSO4, and evaporated in vacuo, subsequently. The residue was recrystallized from diethyl ether to give (R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)-(E)-acryloyl]-3-piperidinecarboxylic acid as a white solid (3.07 g).
Workup
- customthe solvent was evaporated in vacuo
- washThe whole was washed with water, brine
- dry with materialdried over MgSO4
- customevaporated in vacuo
- customThe residue was recrystallized from diethyl ether
Sources & evidence
- ORD record
- ord-e4a155b003454d9f9708f32ecab8adce
- Source dataset
- uspto-grants-2002_05
- Patent number
- US06384028B1
Reaction notes
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