Sodium Hydroxide → 1-Boc-pyrrolidine-3-acetic acid

HRID 1795075Notes

Reaction equation

HRID 1795075 reaction equation
C[O:2][C:3](=[O:17])[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6]1.[OH-].[Na+]>CO>[C:13]([O:12][C:10]([N:7]1[CH2:8][CH2:9][CH:5]([CH2:4][C:3]([OH:17])=[O:2])[CH2:6]1)=[O:11])([CH3:16])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22184663Tert-butyl 3-(2-methoxy-2-oxoethyl)pyrrolidine-1-carboxylate

Product 1

HCID 43437711-Boc-pyrrolidine-3-acetic acidYield 91.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6.6 g (27.13 mmol ) of tert-butyl 3-(2-methoxy-2-oxoethyl)pyrrolidine-1-carboxylate in methanol (150 mL) was added 25 mL (50 mmol) of 2N aqueous NaOH dropwise and the mixture was stirred at room temperature overnight. The solvent was removed under vacuum and the residue was acidified with 2N hydrochloric acid at 0° C. The organics were extracted with ethyl acetate (×3), washed with brine, dried over anhydrous Na2SO4, and filtered. Evaporation of the solvent gave 5.67 g of [1-(tert-butoxycarbonyl)-pyrrolidin-3-yl]acetic acid. The acid (5.64 g, 24.6 mmol) was converted to the title compound (4.2 g) in 3 steps using the procedure outlined in Example 6. 1H NMR (500 MHz, CDCl3) δ 3.64–3.53 (m, 3H), 3.32 (m, 1H), 3.20 (m, 1H), 2.59 (m, 1H), 2.21 (m, 1H), 1.81 (m 1H), 1.49 (s, 9H).

Workup

  1. customThe solvent was removed under vacuum
  2. customwas acidified with 2N hydrochloric acid at 0° C
  3. extractionThe organics were extracted with ethyl acetate (×3)
  4. washwashed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-cb725cd245864f13844a9586066a1644
Source dataset
uspto-grants-2006_04
Patent number
US07026316B2

Reaction notes

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