Sodium Hydroxide → (2S)-1-(tert-Butoxycarbonyl)-2-methylpyrrolidine-2-carboxylic acid

HRID 350379Notes

Reaction equation

HRID 350379 reaction equation
C[O:2][C:3](=[O:17])[C@:4]1([CH3:16])[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[OH-].[Na+]>C1COCC1.O>[C:12]([O:11][C:9]([N:5]1[CH2:6][CH2:7][CH2:8][C@@:4]1([CH3:16])[C:3]([OH:17])=[O:2])=[O:10])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 594364261-tert-Butyl 2-methyl (2S)-2-methylpyrrolidine-1,2-dicarboxylate

Product 1

HCID 11206950(2S)-1-(tert-Butoxycarbonyl)-2-methylpyrrolidine-2-carboxylic acidYield 57%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-tert-butoxycarbonyl-2-methylproline methyl ester (3.20 g, 0.0131 mol) in THF (20 mL) was added 1 N NaOH (15.7 mL) at room temp. After the resulting mixture was stirred for 24 hr, the mixture was diluted with water and washed with EtOAc. The separated aqueous layer was acidified by the addition of 1 N HCl, and extracted with EtOAc. The extract was dried over Na2SO4 and evaporated in vacuo to afford 1.71 g(57%) N-tert-butoxycarbonyl-2-methylproline as a yellow syrup. 1H-NMR (CDCl3) δ 1.42 (s, 9H), 1.48 (s, 3H), 1.88–2.31 (m, 4H), 3.34–3.57 (m, 2H), 9.35 (br s, 1H)

Workup

  1. washwashed with EtOAc
  2. additionThe separated aqueous layer was acidified by the addition of 1 N HCl
  3. extractionextracted with EtOAc
  4. dry with materialThe extract was dried over Na2SO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-50f068ff4a27469ead3f041eebb2af8a
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

Loading…