Hydrochloric Acid → 2-Benzylpyrrolidine

HRID 1045701

Reaction equation

HRID 1045701 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O)(C)(C)C.Cl>C(OCC)(=O)C>[CH2:13]([CH:9]1[CH2:10][CH2:11][CH2:12][NH:8]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 3265841(2RS)-2-benzyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 3395562-BenzylpyrrolidineYield 94.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of (2RS)-2-benzyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1.21 g, 4.6 mmol) in ethyl acetate (20 ml) was added hydrogen chloride (4N) in ethyl acetate (20 ml) at room temperature. The mixture was stirred at room temperature for 2 hours and was concentrated. The residue was partitioned between aqueous sodium hydrogen carbonate and chloroform, and the organic layer was dried over sodium sulfate. The solvent was evaporated under reduced pressure to afford (2RS)-2-benzyl-pyrrolidine (0.7 g, 93%).

Workup

  1. concentrationwas concentrated
  2. customThe residue was partitioned between aqueous sodium hydrogen carbonate and chloroform
  3. dry with materialthe organic layer was dried over sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-68f54c6d5a424369b8b935b679581ef7
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Linked notes

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