Lithium Hydroxide → HCID 40985409, compound

HRID 58890Notes

Reaction equation

HRID 58890 reaction equation
[Li+].[OH-].[CH3:3][O:4][C:5]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:6]=1[CH2:7][N:8]1[C:12](=[O:13])[CH2:11][C@@H:10]([C:14]([O:16]C)=[O:15])[CH2:9]1>C1COCC1.O>[CH3:3][O:4][C:5]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:6]=1[CH2:7][N:8]1[C:12](=[O:13])[CH2:11][C@@H:10]([C:14]([OH:16])=[O:15])[CH2:9]1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 117691043HCID 117691043, compound

Product 1

HCID 40985409HCID 40985409, compoundYield 90.7%

Reagents, catalysts & solvents 1

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

Procedure

LiOH (1.36 g, 32.5 mmol) was added to a solution of (R)-methyl 1-(2,4-dimethoxybenzyl)-5-oxopyrrolidine-3-carboxylate (3.18 g, 10.9 mmol) in THF/H2O (1:1, 40 mL) at 0° C. and the reaction mixture was stirred for 1 h. THF was removed and the remaining aqueous solution was washed with diethyl ether (50 mL×2). The aqueous phase was adjusted to pH=5 with 3 N aqueous HCl and the resulting mixture was extracted with DCM (40 ml×3). The combined extracts were washed with water (100 mL×3) and brine (100 mL×1), dried over anhydrous sodium sulfate and concentrated to afford compound (R)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidine-3-carboxylic acid (2.76 g, 88% yield) as a colorless solid. (S)-1-(2,4-dimethoxybenzyl)-5-oxopyrrolidine-3-carboxylic acid was prepared using the same method.

Workup

  1. customTHF was removed
  2. washthe remaining aqueous solution was washed with diethyl ether (50 mL×2)
  3. extractionthe resulting mixture was extracted with DCM (40 ml×3)
  4. washThe combined extracts were washed with water (100 mL×3) and brine (100 mL×1)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ba39b1f2e5784110a13983a6297909ce
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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