Sodium Hydroxide → (2S,4S)-1-(Tert-butoxycarbonyl)-4-(2-naphthyloxy)-2-pyrrolidinecarboxylic acid

HRID 350477Notes

Reaction equation

HRID 350477 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH2:10][C@H:9]1[C:24]([O:26]C)=[O:25])=[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:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH2:10][C@H:9]1[C:24]([OH:26])=[O:25])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67406330(2S,4S)-1-tert-Butyl 2-methyl 4-(naphthalen-2-yloxy)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 2756011(2S,4S)-1-(Tert-butoxycarbonyl)-4-(2-naphthyloxy)-2-pyrrolidinecarboxylic acidYield 85.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl (2S, 4S)-1-tert-butoxycarbonyl-4-(2-naphthyloxy)-2-pyrrolidinyl carboxylate (5.37 g) in THF (116 ml) was added 0.25 N NaOH (116 ml, 29.0 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 with n-hexane-CHCl3, to give (2S, 4S)-1-tert-butoxycarbonyl-4-(2-naphthyloxy)-2-pyrrolidinylcarboxylic acid [4.44 g, 85%(2 steps)] as a white powder. 1H-NMR (DMSO-d6) δ 1.37 and 1.41 (s, 9H, amide isomers), 2.26 (d, J=13.9 Hz, 1H), 2.65 (m, 1H), 3.47 (d, J=11.5 Hz, 1H), 3.81 (m, 1H), 4.30 (m, 1H), 5.14 (m, 1H), 7.02–7.86 (m, 7H).

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 with n-hexane-CHCl3

Sources & evidence

ORD record
ord-caf4b37178b54c3aaaae86c7537f4c8b
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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