Sodium Hydroxide → 1-((Tert-butoxy)carbonyl)-3-methylpyrrolidine-3-carboxylic acid

HRID 1945494Notes

Reaction equation

HRID 1945494 reaction equation
C[O:2][C:3]([C:5]1([CH3:17])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6]1)=[O:4].[OH-].[Na+]>>[C:13]([O:12][C:10]([N:7]1[CH2:8][CH2:9][C:5]([CH3:17])([C:3]([OH:4])=[O:2])[CH2:6]1)=[O:11])([CH3:16])([CH3:14])[CH3:15]

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 113340041-Tert-butyl 3-methyl 3-methylpyrrolidine-1,3-dicarboxylate

Product 1

HCID 532554551-((Tert-butoxy)carbonyl)-3-methylpyrrolidine-3-carboxylic acidYield 100%

Procedure

To a solution of 3-methylpyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (370 mg, 1.52 mmol) in IMS (5 mL) was added a 1M aqueous solution of sodium hydroxide (2.0 mL, 2.0 mmol). The reaction mixture was stirred at room temperature for 2 hours, and then concentrated under reduced pressure. The residue was partitioned between EtOAc and a 0.1M aqueous solution of HCl. The organic layer was separated and washed with brine, dried over Na2SO4, filtered and concentrated to give the desired product as a white solid (348 mg, 100%). 1H NMR (400 MHz, CHCl3-d): δ 3.85-3.75 (m, 1 H); 3.52-3.41 (m, 2 H); 3.27-3.15 (m, 1 H); 2.39-2.30 (m, 1 H); 1.83-1.74 (m, 1 H); 1.51-1.40 (m, 9 H); 1.38 (s, 3 H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-52882792882447c99640e51981c9b605
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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