Imidazole → HCID 14613761, compound

HRID 2080688Notes

Reaction equation

HRID 2080688 reaction equation
N1C=CN=C1.[C:6]([Si:10]([CH3:13])([CH3:12])Cl)([CH3:9])([CH3:8])[CH3:7].CN(C)C=O.[OH:19][CH:20]1[CH2:24][CH2:23][NH:22][C:21]1=[O:25]>O>[Si:10]([O:19][CH:20]1[CH2:24][CH2:23][NH:22][C:21]1=[O:25])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 102407723-Hydroxy-2-pyrrolidinone

Product 1

HCID 14613761HCID 14613761, compoundYield 11.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In an ice bath, 300 mg of imidazole and 497 mg of tert-butyldimethylchlorosilane were added to a dimethylformamide (2 ml) solution of 255 mg of 3-hydroxypyrrolidin-2-one, and stirred for 1 hour. Water was added to the reaction liquid, extracted with ethyl acetate, and washed with hydrochloric acid (1 N) and saturated saline water. The organic layer was dried to obtain 370 mg of a crude product. 208 g of the product was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=9/1 to 2/8) to obtain 62 mg of the entitled compound as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with hydrochloric acid (1 N) and saturated saline water
  3. customThe organic layer was dried
  4. customto obtain 370 mg of a crude product
  5. custom208 g of the product was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=9/1 to 2/8)

Sources & evidence

ORD record
ord-f423ecac705f4a0a800404723fc9105e
Source dataset
uspto-grants-2011_04
Patent number
US07932394B2

Reaction notes

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