Water → (2S,4S)-4-azido-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid

HRID 1361332Notes

Reaction equation

HRID 1361332 reaction equation
[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]=[N+:14]=[N-:15])[CH2:10][C@H:9]1[C:16]([O:18]C)=[O:17])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O.[Li+].[OH-]>CO>[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]=[N+:14]=[N-:15])[CH2:10][C@H:9]1[C:16]([OH:18])=[O:17])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 11219435(2S,4S)-1-tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylate

Product 1

HCID 12094910(2S,4S)-4-azido-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acidYield 100.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl (2S,4S)-1-Boc-4-azidopyrrolidine-2-carboxylate (10 g, 37 mmol) prepared in Step D of Preparation Example A1-1 in methanol (100 ml) and water (100 ml) was added LiOH (2.5 g, 111 mmol). The solution was stirred at rt for 3 h, concentrated in vacuo, acidified with 1N HCl, and extracted with EtOAC. The organic extracts were washed with brine, dried over MgSO4, and concentrated in vacuo to give the title compound (9.5 g, 95%).

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with EtOAC
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f2e7c218522545d8b7b6339976c17a32
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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