Methanol → 2-Methyl 1-(phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

HRID 2371395Notes

Reaction equation

HRID 2371395 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][C@H:17]([OH:19])[CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[OH-].[Na+].[CH3:27]O>>[CH3:27][O:14][C:13](=[O:15])[C@@H:12]1[CH2:16][C@@H:17]([OH:19])[CH2:18][N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10]

Participants

5

Reactant 4

HCID 887Methanol2×HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 3915171-(Phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

Product 1

HCID 6884112-Methyl 1-(phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

Procedure

To a solution of trans-1-benzyloxycarbonyl-4-hydroxy-L-proline (138 g) in methanol (1380 ml), conc. sulfuric acid (9.92 g) was added, and the resultant mixture was refluxed for 2 hours. The reaction mixture was neutralized with 1N aqueous sodium hydroxide solution, and methanol was removed therefrom. The residue was diluted with ethyl acetate, washed with aqueous sodium chloride solution and dried over magnesium sulfate. Removal of the solvent gave trans-1-benzyloxycarbonyl-4-hydroxy-L-proline methyl ester.

Workup

  1. customwas removed
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-73231abea0e747efbd4cafd51bc67392
Source dataset
uspto-grants-1992_03
Patent number
US05093328

Reaction notes

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