Imidazole → (2R,3S)-3-tert-butyldimethylsilanyloxy-2-methylpyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl Ester

HRID 1864690Notes

Reaction equation

HRID 1864690 reaction equation
[CH3:1][O:2][C:3]([C@@:5]1([CH3:18])[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:24](Cl)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>C(Cl)Cl>[CH3:1][O:2][C:3]([C@@:5]1([CH3:18])[C@@H:9]([O:10][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[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 57974643(2R,3S)-3-Hydroxy-2-methylpyrrolidine-1,2-dicarboxylic Acid 1-tert-butyl Ester 2-methyl Ester

Product 1

HCID 57974635(2R,3S)-3-tert-butyldimethylsilanyloxy-2-methylpyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl EsterYield 61.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 3A (0.591 g, 2.27 mmol) in CH2Cl2 (6.5 mL) at rt was added imidazole (0.464 g, 6.81 mmol) followed by tert-butydimethylsilyl chloride (1.71 g, 11.4 mmol). After stirring overnight, the reaction mixture was partitioned between H2O and CH2Cl2. The CH2Cl2 layer was washed with 1 M H3PO4 and water, then dried (MgSO4), filtered and concentrated under reduced pressure. The residue was chromatographed (silica gel) eluting with 30% EtOAc/hexane to yield compound 3B (0.519 g). LC/MS m/z 396 [M+Na]+.

Workup

  1. customthe reaction mixture was partitioned between H2O and CH2Cl2
  2. washThe CH2Cl2 layer was washed with 1 M H3PO4 and water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed (silica gel)
  7. washeluting with 30% EtOAc/hexane

Sources & evidence

ORD record
ord-dd013c71263f46c59339bb49eba025cb
Source dataset
uspto-grants-2009_12
Patent number
US07625923B2

Reaction notes

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