Sodium Hydroxide → (2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid

HRID 2071115Notes

Reaction equation

HRID 2071115 reaction equation
[OH-].[Na+].C[C@:4]1([C:16]([O-:18])=[O:17])[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]>C1COCC1.CO>[C:12]([O:11][C:9]([N:5]1[CH2:6][CH2:7][CH2:8][C@@H:4]1[C:16]([OH:18])=[O:17])=[O:10])([CH3:15])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 41097300HCID 41097300, compound

Product 1

HCID 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidYield 64%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1N NaOH (1.2 ml, 1.2 mmol, 1.2 eq) was added to a stirred solution of (R)-1-tert-butyl 2-methylpyrrolidine-1,2-dicarboxylate (0.267 g, 1.0 mmol, 1 eq) in 4 ml of 3:1 THF/MeOH. After stirring overnight the solvent was removed in vacuo. The residue was dissolved in saturated aqueous NaHCO3 and extracted with Et2O (×2). The aqueous layer was adjusted to pH {tilde over ( )} 4 with 1N HCl and extracted with EtOAc (×4). The combined EtOAc fractions were dried over Na2SO4. The inorganics were filtered off, and the solvent removed in vacuo yielding 0.1615 g (0.64 mmol, 64% yield) of (R)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid.

Workup

  1. customwas removed in vacuo
  2. dissolutionThe residue was dissolved in saturated aqueous NaHCO3
  3. extractionextracted with Et2O (×2)
  4. extractionextracted with EtOAc (×4)
  5. dry with materialThe combined EtOAc fractions were dried over Na2SO4
  6. filtrationThe inorganics were filtered off
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-0bde89b76a4548539dc89a7a9b6a0cec
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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