Sodium Hydroxide → 1-(Tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid

HRID 354394Notes

Reaction equation

HRID 354394 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][CH:8]([F:10])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4].[OH-].[Na+]>CO>[C:14]([O:13][C:11]([N:6]1[CH2:7][CH:8]([F:10])[CH2:9][CH:5]1[C:3]([OH:4])=[O:2])=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11608471Methyl1-tert-butoxycarbonyl-4-fluoropyrrolidine-2-carboxylate

Product 1

HCID 47125231-(Tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acidYield 97.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl-1-tert-butoxycarbonyl-4-fluoropyrrolidine-2-carboxylate (1.2 g, 4.85 mmol) in MeOH (5 ml) was added 1N NaOH (5 ml) and the mixture was stirred at room temperature for 1 hr. The mixture was concentrated in vacuo, water was added thereto, and neutralized with 1N HCl. The mixture was extracted with EtOAc. The extract was washed with water, then dried over Na2SO4, and concentrated in vacuo to give 1-tert-butoxycarbonyl-4-fluoropyrrolidine-2-carboxylic acid (1.1 g, quant) as a colorless oil. 1H-NMR (CDCl3) δ1.47 (br s, 9H), 2.78-2.83 (br s, 3H), 4.37 (s, 2H), 6.73-6.76 (m, 3H), 7.17 (m, 1H).

Workup

  1. concentrationThe mixture was concentrated in vacuo, water
  2. additionwas added
  3. extractionThe mixture was extracted with EtOAc
  4. washThe extract was washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e7a988f539054eae9b97afed5b8650a9
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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