Lithium Hydroxide → 1-Benzyl-4-(benzylamino)-pyrrolidine-2-carboxylic acid

HRID 490581Notes

Reaction equation

HRID 490581 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][CH:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][N:6]1[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:4].[Li+].[OH-]>C1COCC1.O>[CH2:18]([N:6]1[CH2:7][CH:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][CH:5]1[C:3]([OH:4])=[O:2])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 675488361-Benzyl-4-(benzylamino)-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 675466961-Benzyl-4-(benzylamino)-pyrrolidine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

1-Benzyl-4-(benzylamino)-pyrrolidine-2-carboxylic acid methyl ester and LiOH are dissolved in THF/H2O, and then stirred overnight. After removal of solvent, the residue is neutralized to PH=6-7, and then extracted by EA. The organic layer is washed with water and brine, dried, and concentrated to afford 1-benzyl-4-(benzylamino)-pyrrolidine-2-carboxylic acid (4).

Workup

  1. customAfter removal of solvent
  2. extractionextracted by EA
  3. washThe organic layer is washed with water and brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6fbd808a1da84d5aaba72313f0278eb6
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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