Hydrochloric Acid → 3-Phenylpyrrolidine
Reaction equation
Cl.C(OC([N:9]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10]1)=O)(C)(C)C>C(OCC)(=O)C>[C:14]1([CH:11]2[CH2:12][CH2:13][NH:9][CH2:10]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Hydrogen chloride (4N) in ethyl acetate (6 ml) was added to a solution of 1-tertbutoxycarbonyl-3-phenyl-pyrrolidine (1.84 g, 7.4 mmol) in ethyl acetate (2 ml) and the mixture was stirred for 2 hours. After azeotropical removal of the solvent and hydrogen chloride, the residue was partitioned between aqueous potassium carbonate and diethyl ether, and the organic layer was washed with brine, and dried over sodium sulfate. Removal of the solvent afforded 3-phenyl-pyrrolidine (0.95 g, 87%).
Workup
- customAfter azeotropical removal of the solvent and hydrogen chloride
- customthe residue was partitioned between aqueous potassium carbonate and diethyl ether
- washthe organic layer was washed with brine
- dry with materialdried over sodium sulfate
- customRemoval of the solvent
Sources & evidence
- ORD record
- ord-488288d0781a4f578c13ada92f70da69
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569294B2
Reaction notes
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