Sodium Hydroxide → (S)-2-(1-BOC-2-pyrrolidinyl)acetic acid

HRID 458476

Reaction equation

HRID 458476 reaction equation
C[O:2][C:3](=[O:17])[CH2:4][C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[OH-].[Na+]>CO>[C:13]([O:12][C:10]([N:6]1[CH2:7][CH2:8][CH2:9][C@H:5]1[CH2:4][C:3]([OH:17])=[O:2])=[O:11])([CH3:16])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11075654METHYL (2S)-PYRROLIDIN-2-YLACETATE

Product 1

HCID 688605(S)-2-(1-BOC-2-pyrrolidinyl)acetic acidYield 92.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl (2S)-2-(2-methoxy-2-oxoethyl)-1-pyrrolidinecarboxylate (8.35 g, 34.3 mmol) was dissolved in 150 mL MeOH. Aqueous NaOH (50 mL, 1 M) was added and the reaction mixture was allowed to stand overnight. After concentration in vacuo to ca. 100 mL, the solution was added to 300 mL water and extracted with ether (2×). The carboxylate solution was acidified to pH 2 with 12 N HCl and extracted with ether (2×). The aqueous layer was saturated with salt and extracted a third time with ether. The combined organic layers were washed with water, brine and dried over MgSO4. Filtration and concentration provided the title acid as a white solid (7.28 g, 31.7 mmol, 92.6%): 1H NMR (300 MHz, CDCl3, mixture of rotamers) δ 4.16 (bs, 1H), 3.37 (bs, 2H), 3.0–2.8 (bs, 1H), 2.36 (dd, J=9.3, 15.3 Hz, 1H), 2.2–2.0 (m, 1H), 1.9–1.7 (m, 4H), 1.48 (s, 9H) ppm.

Workup

  1. concentrationAfter concentration in vacuo to ca. 100 mL
  2. additionthe solution was added to 300 mL water
  3. extractionextracted with ether (2×)
  4. extractionextracted with ether (2×)
  5. extractionextracted a third time with ether
  6. washThe combined organic layers were washed with water, brine
  7. dry with materialdried over MgSO4
  8. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-105dda33601e4642bccaad5f98c8e52b
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Linked notes

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