(Diethylamino)sulfur trifluoride → 4-(4-Fluoropiperidin-1-yl)benzoic acid ethyl ester

HRID 1626286Notes

Reaction equation

HRID 1626286 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][CH:14](O)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)[CH3:2].CCN(S(F)(F)[F:25])CC>ClCCl>[CH2:1]([O:3][C:4](=[O:18])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][CH:14]([F:25])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 12717445Ethyl 4-(4-hydroxypiperidin-1-yl)benzoate

Product 1

HCID 686494674-(4-Fluoropiperidin-1-yl)benzoic acid ethyl esterYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(4-hydroxy-piperidin-1-yl)benzoic acid ethyl ester (1.25 g. 5 mmoles) in dry dichloromethane (30 ml) at room temperature under an inert atmosphere, it was slowly added DAST (0.97 g, 6 mmoles) in dichloromethane (5 ml). The reaction mixture was stirred at room temperature for 1 hour and then quenched with aqueous NaHCO3. The organic layer was washed with brine, dried and evaporated. The residue was purified by flash chromatography on silica gel using hexane/EtOAc (70/30) as eluent to give the title compound as a white solid (0.7 g, 56%).

Workup

  1. customat room temperature
  2. customquenched with aqueous NaHCO3
  3. washThe organic layer was washed with brine
  4. customdried
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-de45acf65dcb49d29dc5a4e61d575c78
Source dataset
uspto-grants-2014_07
Patent number
US08785448B2

Reaction notes

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