1-Pyrrolidineacetic acid, ethyl ester → Pyrrolidin-1-ylacetic acid

HRID 64066

Reaction equation

HRID 64066 reaction equation
[N:1]1([CH2:6][C:7]([O:9]CC)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1>Cl>[N:1]1([CH2:6][C:7]([OH:9])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 2109961-Pyrrolidineacetic acid, ethyl ester

Product 1

HCID 414564Pyrrolidin-1-ylacetic acidYield 91%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The solution of ethyl 2-(pyrrolidin-1-yl)acetate (2 g, 12.7 mmol, 1.0 eq) in 8 N HCl was stirred at 95° C. for 16 h. The mixture was concentrated and quenched and extracted as in Intermediate Example 15(b). The solvent was distilled off to afford the product in 91% yield (1.5 g). LC-MS (ESI): Calculated mass: 129.1; Observed mass 130.1 [M+H+] (rt: 0.26 min).

Workup

  1. concentrationThe mixture was concentrated
  2. customquenched
  3. extractionextracted as in Intermediate Example 15(b)
  4. distillationThe solvent was distilled off
  5. customto afford the product in 91% yield (1.5 g)
  6. customObserved mass 130.1 [M+H+] (rt: 0.26 min)

Sources & evidence

ORD record
ord-4fed8b6380b94254a92f74f824b0f9b3
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Linked notes

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