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

HRID 64078

Reaction equation

HRID 64078 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 54%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The solution of ethyl 2-(pyrrolidin-1-yl)acetate (1.8 g, 11.95 mmol, 1.0 eq) in 8 N HCl was stirred at 95° C. for 16 h. The mixture was concentrated on vacuum pump and quenched and extracted as in Intermediate Example 15(b). The solvent was distilled off to afford the product in 54% yield (1.4 g). LC-MS (ESI): Calculated mass: 129.1; Observed mass 130.1 [M+H]+ (rt: 0.26 min).

Workup

  1. concentrationThe mixture was concentrated on vacuum pump
  2. customquenched
  3. extractionextracted as in Intermediate Example 15(b)
  4. distillationThe solvent was distilled off
  5. customto afford the product in 54% yield (1.4 g)
  6. customObserved mass 130.1 [M+H]+ (rt: 0.26 min)

Sources & evidence

ORD record
ord-51539287a7fb4cb9b67dc53ad3804551
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Linked notes

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