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

HRID 354317Notes

Reaction equation

HRID 354317 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 (20mL) was added 1N 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 1N 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) δ1.42 (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 1N HCl
  3. extractionextracted with EtOAc
  4. dry with materialThe extract was dried over Na2SO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-fe164b270ce94e50b491f2cacbc22cff
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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