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

HRID 350458Notes

Reaction equation

HRID 350458 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 methyl1-tert-butoxycarbonyl-4-fluoropyrrolidine-2-carboxylate(1.2 g, 4.85 mmol) in MeOH (5 ml) was added 1 N 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 1 N 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) δ 1.47 (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-311d71a5a8774a18bc7ea0b299c8027b
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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