Imidazole → HCID 15671472, compound

HRID 1088264Notes

Reaction equation

HRID 1088264 reaction equation
[N+:1]([C:4]1[CH:29]=[CH:28][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@H:15]([O:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][C@H:13]2[CH2:26][OH:27])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].N1C=CN=C1.[Si:35](Cl)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36]>CN(C)C=O.C(OCC)(=O)C>[N+:1]([C:4]1[CH:29]=[CH:28][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@H:15]([O:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][C@H:13]2[CH2:26][O:27][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 14830186HCID 14830186, compound

Product 1

HCID 15671472HCID 15671472, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2S,4R)-1-(p-Nitrobenzyloxycarbonyl)-2-hydroxymethyl-4-benzoyloxypyrrolidine (1.09 g), imidazole (0.46 g) and t-butyldimethylsilyl chloride (0.49 g) were dissolved in 16.5 ml of dry dimethylformamide. The resulting mixture was stirred at room temperature for 2 hours, diluted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate and distilled to remove the solvent. The residue was purified by silica gel chromatography to obtain (2S,4R)-1-(p-nitrobenzyloxycarbonyl)-2-t-butyldimethylsilyloxymethyl-4-benzoyloxypyrrolidine.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationdistilled
  4. customto remove the solvent
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8025d30a0ee54c038d716cfa5cb23e9e
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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