Sodium Hydroxide → 1-(4-Fluorobenzoyl)pyrrolidine-2-carboxylic acid

HRID 586623

Reaction equation

HRID 586623 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].[OH-].[Na+].[F:11][C:12]1[CH:20]=[CH:19][C:15]([C:16](Cl)=[O:17])=[CH:14][CH:13]=1>Cl>[F:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([N:1]2[CH2:8][CH2:7][CH2:6][CH:2]2[C:3]([OH:5])=[O:4])=[O:17])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 678794-Fluorobenzoyl chlorideHCID 145742L-Proline

Product 1

HCID 123676841-(4-Fluorobenzoyl)pyrrolidine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

L-Proline (2.5 g, 22 mmol) is dissolved in NaOH (5%, 25 ml, 31 mmol) and, after cooling, treated dropwise, with vigorous stirring, with 4-fluorobenzoyl chloride (3.17 g, 20 mmol). The resulting suspension is again treated with NaOH (5%, 15 ml, 19 mmol) and stirred at RT for 1 h. HCl (20% strength, 10 ml) is added with ice cooling and the mixture is stirred until formation of a crystallizate which can be filtered off with suction. The crystallizate subsequently filtered off with suction is washed with water until HCl-free and dried over P2O5 in a desiccator. 4.21 g (88.8% of theory) of crystallizate remain after drying.

Workup

  1. temperatureafter cooling
  2. stirringthe mixture is stirred until formation of a crystallizate which
  3. filtrationcan be filtered off with suction
  4. filtrationThe crystallizate subsequently filtered off with suction
  5. washis washed with water until HCl-free
  6. dry with materialdried over P2O5 in a desiccator
  7. customafter drying

Sources & evidence

ORD record
ord-e18216b60fd04c46abd76b3fc75fec71
Source dataset
uspto-grants-2005_08
Patent number
US06936632B2

Linked notes

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