Imidazole → 1-(Phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

HRID 968937Notes

Reaction equation

HRID 968937 reaction equation
C[O:2][C:3](=[O:17])[C@@H:4]1[CH2:8][C@@H:7]([OH:9])[CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:16])(C)C)=[O:11].N1[CH:22]=[CH:21]N=C1.[Si](Cl)([C:26](C)([CH3:28])[CH3:27])(C)C>CN(C=O)C>[OH:9][C@H:7]1[CH2:6][N:5]([C:10]([O:12][CH2:13][C:16]2[CH:22]=[CH:21][CH:28]=[CH:26][CH:27]=2)=[O:11])[C@H:4]([C:3]([OH:2])=[O:17])[CH2:8]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 2734883(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Product 1

HCID 3915171-(Phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylateYield 120.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Boc-trans-4-hydroxy-L-proline methyl ester (10.35 g, 0.04 mol) was dissolved in DMF (135 mL). Imidazole (13.6 g, 0.20 mol) was added, followed by the addition of tert-butyldimethylsilyl chloride (18.1 g, 0.12 mol) and the solution was stirred overnight at room temperature. DMF was removed via vacuum rotary evaporation and the residue was dissolved in ethyl acetate. The solution was washed with 1M HCl and brine. The organic solution was dried over MgSO4 and concentrated. The crude product was purified by column chromatography eluting with hexanes/ethyl acetate (4/1, v/v) to afford 12.83 g (89% yield) of the desired product 1 as a colorless oil.

Workup

  1. customDMF was removed via vacuum rotary evaporation
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe solution was washed with 1M HCl and brine
  4. dry with materialThe organic solution was dried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography
  7. washeluting with hexanes/ethyl acetate (4/1

Sources & evidence

ORD record
ord-7477d1dd044a44ae878b7d809fbddcbf
Source dataset
uspto-grants-2007_12
Patent number
US07304165B2

Reaction notes

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