Lithium Hydroxide → HCID 86723602, compound

HRID 590666Notes

Reaction equation

HRID 590666 reaction equation
[CH2:1]([CH:3]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@H:5]([C:15]([O:17]C)=[O:16])[CH2:4]1)[CH3:2].[Li+].[OH-]>CO>[C:11]([O:10][C:8]([N:6]1[CH2:7][CH:3]([CH2:1][CH3:2])[CH2:4][C@H:5]1[C:15]([OH:17])=[O:16])=[O:9])([CH3:12])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 15719911HCID 15719911, compound

Product 1

HCID 86723602HCID 86723602, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (2S)-1-tert-butyl 2-methyl 4-ethylpyrrolidine-1,2-dicarboxylate (49.5 g, 0.19 mol), LiOH (950 mL, 1M) in MeOH (1500 mL) was stirred at room temperature overnight. TLC showed the reaction was completed. The mixture was concentrated, adjusted the pH to 2 with 1N HCl. The mixture was extracted with EA, the combined organic layer was washed with brine, dried over Na2SO4, concentrated to afford (2S)-1-(tert-butoxycarbonyl)-4-ethylpyrrolidine-2-carboxylic acid (45.5 g, 97%) as white solid without further purification.

Workup

  1. concentrationThe mixture was concentrated
  2. extractionThe mixture was extracted with EA
  3. washthe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-992354724f5a487caa6be83c51616e2e
Source dataset
uspto-grants-2016_01
Patent number
US09233974B2

Reaction notes

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