Lithium Hydroxide → (2S)-1-(Benzenesulfonyl)pyrrolidine-2-carboxylic acid

HRID 460272Notes

Reaction equation

HRID 460272 reaction equation
C[O:2][C:3](=[O:18])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:11])=[O:10].[Li+].[OH-]>CO>[C:12]1([S:9]([N:5]2[CH2:6][CH2:7][CH2:8][C@H:4]2[C:3]([OH:18])=[O:2])(=[O:11])=[O:10])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 720698N-(benzenesulfonyl)-Proline methyl ester

Product 1

HCID 720844(2S)-1-(Benzenesulfonyl)pyrrolidine-2-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 38.2 g (0.142 mol) of the above methyl ester 7 in 500 mL methanol was added 140 mL (0.28 mol) of freshly-prepared 2 M aqueous LiOH with stirring to give a colorless solution. This was stirred overnight, after which HPLC showed no starting material. The solution was reduced by 50% in vacuo and partitioned between 1 N HCl and CH2Cl2 (˜200 mL each). The phases were separated and the aqueous layer was washed again with CH2Cl2. The organic phases were combined, dried (MgSO4), and concentrated to a white solid. This was recrystallized twice from ethyl acetate/hexanes to give 34.7 g (0.136 mol, 96%) of 8 as fine white needles. M/z=256.2 (M+H+).

Workup

  1. customto give a colorless solution
  2. stirringThis was stirred overnight
  3. custompartitioned between 1 N HCl and CH2Cl2 (˜200 mL each)
  4. customThe phases were separated
  5. washthe aqueous layer was washed again with CH2Cl2
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated to a white solid
  8. customThis was recrystallized twice from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-d312fbf8ee9946aea1a0d44804410a96
Source dataset
uspto-grants-2007_03
Patent number
US07196112B2

Reaction notes

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