Lithium Hydroxide → 1-[(Benzyloxy)carbonyl]-3-methylpyrrolidine-3-carboxylic acid

HRID 875744Notes

Reaction equation

HRID 875744 reaction equation
[CH3:1][C:2]1([C:17]([O:19]C)=[O:18])[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.[Li+].[OH-]>C(O)C>[CH2:10]([O:9][C:7]([N:4]1[CH2:5][CH2:6][C:2]([CH3:1])([C:17]([OH:19])=[O:18])[CH2:3]1)=[O:8])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 602052351-Benzyl 3-methyl 3-methylpyrrolidine-1,3-dicarboxylate

Product 1

HCID 602052341-[(Benzyloxy)carbonyl]-3-methylpyrrolidine-3-carboxylic acidYield 99.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
78 °C

Procedure

1-Benzyl 3-methyl 3-methylpyrrolidine-1,3-dicarboxylate (2.72 g, 9.81 mmol) in ethanol (15 mL) was added to a 3M LiOH solution (14.7 mL, 29.4 mmol), and the reaction mixture was stirred at 78° C. (bath) for 1 hour. The ethanol was removed and, ether (30 mL) was added. The aqueous layer was separated and acidified with saturated potassium hydrogen sulfate to a pH of about 3 to about 4, extracted with ethyl acetate (50 mL), washed with brine and dried over sodium sulfate. After removal of the solvent, 1-(benzyloxycarbonyl)-3-methylpyrrolidine-3-carboxylic acid (2.56 g, 99% yield) was isolated as an oil.

Workup

  1. customThe ethanol was removed
  2. additionether (30 mL) was added
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate (50 mL)
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. customAfter removal of the solvent

Sources & evidence

ORD record
ord-dafdf9d0a79947219fb62b01ffa2325d
Source dataset
uspto-grants-2015_03
Patent number
US08981085B2

Reaction notes

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