Imidazole → Methyl (2S,3S)-1-Boc-3-[(tert-butyldimethylsilyl)oxy]pyrrolidine-2-carboxylate

HRID 1864694Notes

Reaction equation

HRID 1864694 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[C@@H:9]([OH:10])[CH2:8][CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4].N1C=CN=C1.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>CN(C=O)C>[CH3:1][O:2][C:3]([C@@H:5]1[C@@H:9]([O:10][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH2:8][CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 147292531-tert-butyl 2-methyl (2S,3S)-3-hydroxypyrrolidine-1,2-dicarboxylate

Product 1

HCID 58841066Methyl (2S,3S)-1-Boc-3-[(tert-butyldimethylsilyl)oxy]pyrrolidine-2-carboxylateYield 95.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2S,3S)-N-tert-butyloxycarbonyl-3-hydroxy-2 pyrrolidinecarboxylic acid methyl ester (1B) (4.90 g, 20.0 mmol) in DMF (20 mL) at rt was added imidazole (3.41 g, 50.1 mmol), and then tert-butydimethylsilyl chloride (3.91 g, 25.9 mmol). After stirring at rt overnight, the reaction mixture was partitioned between H2O and CH2Cl2. The CH2Cl2 layer was washed with 1 M H3PO4, saturated aqueous NaHCO3 and brine, dried (MgSO4), then filtered and concentrated under reduced pressure. The residue was chromatographed (silica gel) eluting with 0-20% EtOAc/hexane to yield (2S,3S)-3-(tert-butyldimethylsilanyloxy)pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (6.86 g).

Workup

  1. customthe reaction mixture was partitioned between H2O and CH2Cl2
  2. washThe CH2Cl2 layer was washed with 1 M H3PO4, saturated aqueous NaHCO3 and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed (silica gel)
  7. washeluting with 0-20% EtOAc/hexane

Sources & evidence

ORD record
ord-2ddead420a2048168e7e3b9f60c7f898
Source dataset
uspto-grants-2009_12
Patent number
US07625923B2

Reaction notes

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