Lithium hydroxide, monohydrate → 1,2-Pyrrolidinedicarboxylic acid, 4,4-diMethyl-, 1-(1,1-diMethylethyl) ester, (2R)-

HRID 712812Notes

Reaction equation

HRID 712812 reaction equation
[CH3:1][C:2]1([CH3:24])[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:4]([C:14]([O:16]CC2C=CC=CC=2)=[O:15])[CH2:3]1.O[Li].O>O1CCOCC1.O>[C:10]([O:9][C:7]([N:5]1[CH2:6][C:2]([CH3:24])([CH3:1])[CH2:3][C@@H:4]1[C:14]([OH:16])=[O:15])=[O:8])([CH3:13])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 117966726HCID 117966726, compound

Product 1

HCID 944133841,2-Pyrrolidinedicarboxylic acid, 4,4-diMethyl-, 1-(1,1-diMethylethyl) ester, (2R)-Yield 58.5%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a mixture of (R)-2-benzyl 1-tert-butyl 4,4-dimethylpyrrolidine-1,2-dicarboxylate (D40) (198 mg, 0.59 mmol) in dioxan/water (4/4 ml), LiOH.H2O (100 mg, 2.37 mmol) was added and the mixture was left stirring at RT for 18 hrs. Organic solvent was evaporated off and the reaction mixture was diluted with water (8 ml), washed with Et2O (2×10 ml), acidified with acetic acid to pH˜4-5 and extracted with Et2O (3×10 ml). The organic phases were collected, dried over Na2SO4 and evaporated in vacuo to afford the title compound (D41) (84 mg).

Workup

  1. additionwas added
  2. waitthe mixture was left
  3. customOrganic solvent was evaporated off
  4. additionthe reaction mixture was diluted with water (8 ml)
  5. washwashed with Et2O (2×10 ml)
  6. extractionextracted with Et2O (3×10 ml)
  7. customThe organic phases were collected
  8. dry with materialdried over Na2SO4
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-545b5dc4fe6e4806a1d822e237ee3830
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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