Sodium Hydroxide → (R)-3-amino-1-(4-chlorobenzyl)pyrrolidine

HRID 133553Notes

Reaction equation

HRID 133553 reaction equation
Cl.Cl.[NH2:3][C@@H:4]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH2:5]1.[OH-].[Na+]>C(OCC)(=O)C>[NH2:3][C@@H:4]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH2:5]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53256324(R)-1-(4-Chlorobenzyl)pyrrolidin-3-amine dihydrochloride

Product 1

HCID 24904911(R)-3-amino-1-(4-chlorobenzyl)pyrrolidineYield 99.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (R)-3-amino-1-(4-chlorobenzyl)pyrrolidine dihydrochloride (4.54 g, 16.0 mmol) with a 2 M solution (80 mL) of NaOH and ethyl acetate (80 mL) was stirred, and the organic layer was separated to extract the aqueous layer with ethyl acetate (80 mL×2). The organic layers were combined, dried over anhydrous sodium sulfate, then filtered and concentrated to thereby afford free (R)-3-amino-1-(4-chlorobenzyl)pyrrolidine (3.35 g, 99%).

Workup

  1. customthe organic layer was separated
  2. extractionto extract the aqueous layer with ethyl acetate (80 mL×2)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-313e60a389b64e54ad3b444af3783b72
Source dataset
uspto-grants-2008_06
Patent number
US07390830B1

Reaction notes

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