Lithium Hydroxide → 1-[(Benzyloxy)carbonyl]-3-methylpyrrolidine-3-carboxylic acid
Reaction equation
[Li+].[OH-].[CH3:3][C:4]1([C:19]([O:21]C)=[O:20])[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5]1>C(O)C>[CH2:12]([O:11][C:9]([N:6]1[CH2:7][CH2:8][C:4]([CH3:3])([C:19]([OH:21])=[O:20])[CH2:5]1)=[O:10])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 78 °C
Procedure
A 3M LiOH solution (14.7 mL, 29.4 mmol) was added to 1-benzyl 3-methyl 3-methylpyrrolidine-1,3-dicarboxylate (2.72 g, 9.81 mmol) in ethanol (15 mL), and the reaction mixture was stirred at 78° C. (bath) for 1 hour. The ethanol was removed, and ether (30 mL) was added. The aqueous layer was separated and acidified with saturated potassium hydrogen sulfate to a pH of about 3 to about 4, extracted with ethyl acetate (50 mL), washed with brine and dried over sodium sulfate. After removal of the solvent, 1-(benzyloxycarbonyl)-3-methylpyrrolidine-3-carboxylic acid (2.56 g, 99% yield) was isolated as an oil.
Workup
- customThe ethanol was removed
- additionether (30 mL) was added
- customThe aqueous layer was separated
- extractionextracted with ethyl acetate (50 mL)
- washwashed with brine
- dry with materialdried over sodium sulfate
- customAfter removal of the solvent
Sources & evidence
- ORD record
- ord-df02fc47b4bf478f9f5dcef03b12aaac
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365568B2
Reaction notes
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