Lithium Hydroxide → 1-Benzyl-4-[tert-butoxycarbonyl-(benzyl)-amino]-pyrrolidine-2-carboxylic acid

HRID 490574Notes

Reaction equation

HRID 490574 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][CH:8]([N:10]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][N:6]1[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:4].[Li+].[OH-]>CO>[CH2:25]([N:6]1[CH2:7][CH:8]([N:10]([C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:9][CH:5]1[C:3]([OH:4])=[O:2])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 675488151-Benzyl-4-[tert-butoxycarbonyl-(benzyl)-amino]-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 675493681-Benzyl-4-[tert-butoxycarbonyl-(benzyl)-amino]-pyrrolidine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-benzyl-4-[tert-butoxycarbonyl-(benzyl)-amino]-pyrrolidine-2-carboxylic acid methyl ester (11) in CH3OH is added LiOH, and the solution is stirred overnight at rt. After removal of solvent, the residue is dissolved in water, acidified until PH=5, and then extracted with EA, and concentrated to afford the product 1-benzyl-4-[tert-butoxycarbonyl-(benzyl)-amino]-pyrrolidine-2-carboxylic acid (12).

Workup

  1. customAfter removal of solvent
  2. dissolutionthe residue is dissolved in water
  3. extractionextracted with EA
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-70379a9e633f41f2841f88c31c21350c
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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