Imidazole → HCID 86626207, compound

HRID 2355532Notes

Reaction equation

HRID 2355532 reaction equation
[F:1][C@@H:2]1[C@@H:6]([OH:7])[CH2:5][C@H:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:3]1.[CH3:13][C:14]([Si:17](Cl)([CH3:19])[CH3:18])([CH3:16])[CH3:15].N1C=CN=C1>CN(C=O)C>[Si:17]([O:7][C@@H:6]1[C@@H:2]([F:1])[CH2:3][C@@H:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:5]1)([C:14]([CH3:16])([CH3:15])[CH3:13])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 86626208HCID 86626208, compound

Product 1

HCID 86626207HCID 86626207, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the (1S,3S,4S)-ethyl 3-fluoro-4-hydroxycyclopentanecarboxylate (6.73 g, 38.2 mmol, 1.0 equiv), TBSCl (11.5 g, 76.4 mmol, 2.0 equiv) and imidazole (12 g, 0.17 mol, 4.0 equiv) in DMF (10 mL) was stirred at rt for 4 h. After this time the free alcohol was consumed by tlc analysis. The DMF was removed in vacuo and the residue was partitioned between ether and water. The layers were separated and the organic layer washed with brine, dried over Na2SO4 filtered, and evaporated. (1S,3S,4S)-ethyl 3-(tert-butyldimethylsilyloxy)-4-fluorocyclopentanecarboxylate was isolated in quantitative yield.

Workup

  1. customAfter this time the free alcohol was consumed by tlc analysis
  2. customThe DMF was removed in vacuo
  3. customthe residue was partitioned between ether and water
  4. customThe layers were separated
  5. washthe organic layer washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-6299f5fd422d4cdb956eaf0dc8b45bc6
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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