3-(4-Chloro-benzyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester → 3-((4-Chlorobenzyl)oxy)pyrrolidine

HRID 496225Notes

Reaction equation

HRID 496225 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:9]1)=O)(C)(C)C>C(O)=O>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][O:13][CH:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)=[CH:16][CH:17]=1

Participants

3

Reactant 1

HCID 667576123-(4-Chloro-benzyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 223136933-((4-Chlorobenzyl)oxy)pyrrolidineYield 70%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 3-(4-Chloro-benzyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.28 g, 0.9 mmol) in aqueous 90% formic acid (7.5 mL) was stirred at (0° C.) for 30 min. then at room temperature overnight. The solvents were removed under reduced pressure and the residue was treated with saturated aqueous potassium carbonate and extracted twice with n-butanol. The combined organic extracts was concentrated and the residue was purified by flash chromatography (SiO2, dichloromethane-methanol-ammonium hydroxide, 8:8:1 then 50:10:1) to afford the subtitle compound 3-(4-Chloro-benzyloxy)-pyrrolidine (0.13 g, 70%).

Workup

  1. customat room temperature
  2. customovernight
  3. customThe solvents were removed under reduced pressure
  4. additionthe residue was treated with saturated aqueous potassium carbonate
  5. extractionextracted twice with n-butanol
  6. concentrationThe combined organic extracts was concentrated
  7. customthe residue was purified by flash chromatography (SiO2, dichloromethane-methanol-ammonium hydroxide, 8:8:1

Sources & evidence

ORD record
ord-4391f5edb0524f62aacb4e1e64b16c30
Source dataset
uspto-grants-2005_09
Patent number
US06943188B2

Reaction notes

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