3-Fluoroaniline → 1-(3-Fluorophenyl)-2-oxopyrrolidine-3-carboxylic acid

HRID 58560

Reaction equation

HRID 58560 reaction equation
CC1(C)[O:9][C:8](=[O:10])[C:5]2([CH2:7][CH2:6]2)[C:4](=[O:11])O1.[F:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17]>C(O)C>[F:13][C:14]1[CH:15]=[C:16]([N:17]2[CH2:6][CH2:7][CH:5]([C:8]([OH:9])=[O:10])[C:4]2=[O:11])[CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 97423-FluoroanilineHCID 797206,6-Dimethyl-5,7-dioxaspiro(2.5)octane-4,8-dione

Product 1

HCID 242752371-(3-Fluorophenyl)-2-oxopyrrolidine-3-carboxylic acidYield 85.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6,6-dimethyl-5,7-dioxaspiro[2.5]octane-4,8-dione (0.500 g; 2.94 mmol) and 3-fluoroaniline (0.847 mL; 8.82 mmol) in ethanol (3 mL) was irradiated in a microwave oven for 3 minutes at 100° C. The mixture was concentrated under reduced pressure and the residue was dissolved in a solution of sodium hydroxide 6N, washed with dichloromethane, acidified with a solution of hydrochloric acid 6N to pH=2, extracted with ethyl acetate dried and concentrated under reduced pressure to yield 0.560 g (85%) of a dark orange solid, which was used in the next step without further purification.

Workup

  1. customwas irradiated in a microwave oven for 3 minutes at 100° C
  2. concentrationThe mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in a solution of sodium hydroxide 6N
  4. washwashed with dichloromethane
  5. extractionextracted with ethyl acetate
  6. customdried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e5b3d20c5573445ebaeaff8e0a5eee36
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Linked notes

Loading…