Sodium Hydroxide → (2S,4S)-1-(tert-Butoxycarbonyl)-4-phenoxy-2-pyrrolidinecarboxylic acid

HRID 350463Notes

Reaction equation

HRID 350463 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][C@H:9]1[C:20]([O:22]C)=[O:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:10][C@H:9]1[C:20]([OH:22])=[O:21])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10710901HCID 10710901, compound

Product 1

HCID 2756009(2S,4S)-1-(tert-Butoxycarbonyl)-4-phenoxy-2-pyrrolidinecarboxylic acidYield 58.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl (2S,4S)-1-tert-butoxycarbonyl-4-phenoxy-2-pyrrolidinylcarboxylate (5.31 g, 16.5 mmol) in THF (132 ml) was added 0.25 N NaOH (132 ml, 33.0 mmol) at room temperature. The resulting mixture was stirred over night. After removal of the solvent, the mixture was acidified by the addition of 1 N HCl and extracted with CHCl3. The combined extracts were washed with brine, dried over Na2SO4 and evaporated. The residue was recrystallized from n-hexane-CHCl3, to give (2S, 4S)-1-tert-butoxycarbonyl-4-phenoxy-2-pyrrolidinylcarboxylic acid (2.96 g, 58%) as a white powder. 1H-NMR (DMSO-d6) δ 1.36 (s, 9H), 2.16 (d, J=13.2 Hz, 1H), 2.56 (m, 1H ), 3.46 (m, 1H), 3.71 (dt, J=12.0, 5.4 Hz, 1H), 4.26 (dt, J=9.5, 7.1 Hz, 1H), 4.99 (m, 1H), 6.85 (m, 2H), 6.94 (t, J=7.3 Hz, 1H), 7.28 (t, J=7.3 Hz, 1H).

Workup

  1. customAfter removal of the solvent
  2. additionthe mixture was acidified by the addition of 1 N HCl
  3. extractionextracted with CHCl3
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue was recrystallized from n-hexane-CHCl3

Sources & evidence

ORD record
ord-35b464c5c40d41dbb8173523e88c0c06
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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