Imidazole → HCID 86626207, compound

HRID 1254415Notes

Reaction equation

HRID 1254415 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 alchol 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 alchol 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-40fa0dd13e3b4368b0b2639827464381
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

Loading…