Triethylamine → 2,2,2-Trifluoro-1-(3-hydroxypiperidin-1-yl)ethanone

HRID 602127Notes

Reaction equation

HRID 602127 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.C(N(CC)CC)C.[OH:17][CH:18]1[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]1>C(O)C>[F:9][C:2]([F:1])([F:8])[C:3]([N:20]1[CH2:21][CH2:22][CH2:23][CH:18]([OH:17])[CH2:19]1)=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9794Ethyl trifluoroacetateHCID 232933-Hydroxypiperidine

Product 1

HCID 589925842,2,2-Trifluoro-1-(3-hydroxypiperidin-1-yl)ethanoneYield 85.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl trifluoroacetate (1.31 mL, 11.0 mmol) and triethylamine (1.68 mL, 12.0 mmol) were added to 3-hydroxypiperidine (1.01 g, 10.0 mmol) in ethanol (10 mL). The mixture was stirred at room temperature for 8 hours. Subsequently, the reaction mixture was concentrated and water was added. The mixture was then extracted with ethyl acetate and the extract washed with brine and dried over magnesium sulfate. Purification of the residue by silica gel column chromatography (hexane:ethyl acetate=10:1->2:1) gave 1.68 g (85%) of the desired compound as a colorless oil.

Workup

  1. concentrationSubsequently, the reaction mixture was concentrated
  2. additionwater was added
  3. extractionThe mixture was then extracted with ethyl acetate
  4. washthe extract washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customPurification of the residue by silica gel column chromatography (hexane:ethyl acetate=10:1->2:1)

Sources & evidence

ORD record
ord-b402d2792c5e4687b940034055329816
Source dataset
uspto-grants-2011_03
Patent number
US07902367B2

Reaction notes

Loading…