Sodium Hydroxide → 1-N-Cbz-pyrrolidine-3-carboxylic acid

HRID 2288746Notes

Reaction equation

HRID 2288746 reaction equation
[OH-].[Na+].[C:3]([N:13]1[CH2:17][CH2:16][CH:15]([C:18]([O:20]CCCC)=[O:19])[CH2:14]1)([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4]>CO>[C:3]([N:13]1[CH2:17][CH2:16][CH:15]([C:18]([OH:20])=[O:19])[CH2:14]1)([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18698055HCID 18698055, compound

Product 1

HCID 185384831-N-Cbz-pyrrolidine-3-carboxylic acidYield 69.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aqueous 1M NaOH (6 ml) was added to a stirred solution of the above ester (1.37 g) in MeOH (6 ml). After 1 hour, the methanol was evaporated. H2O (20 ml) was added to the residue and 1M HCl (6 ml) was added dropwise to the stirred mixture. This aqueous phase was extracted with EtOAc (3×25 ml). The combined organic phases were washed with saturated brine (1×20 ml) dried and evaporated to give, as a colourless oil, N-Cbz-3-carboxy pyrrolidine (780 mg);

Workup

  1. customthe methanol was evaporated
  2. additionH2O (20 ml) was added to the residue and 1M HCl (6 ml)
  3. additionwas added dropwise to the stirred mixture
  4. extractionThis aqueous phase was extracted with EtOAc (3×25 ml)
  5. washThe combined organic phases were washed with saturated brine (1×20 ml)
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-def521334be244fdabba24f8966330ad
Source dataset
uspto-grants-2000_07
Patent number
US06090813

Reaction notes

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