Hydrochloric Acid → 3-Phenylpyrrolidine

HRID 1045679Notes

Reaction equation

HRID 1045679 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]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 112303881-Boc-3-Phenyl-pyrrolidine

Product 1

HCID 31467433-PhenylpyrrolidineYield 87.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

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

  1. customAfter azeotropical removal of the solvent and hydrogen chloride
  2. customthe residue was partitioned between aqueous potassium carbonate and diethyl ether
  3. washthe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-488288d0781a4f578c13ada92f70da69
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

Loading…