Ethyl trifluoroacetate → HCID 21993671, compound

HRID 1624873Notes

Reaction equation

HRID 1624873 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.[F:24][C:25]([F:32])([F:31])[C:26](OCC)=[O:27]>C(Cl)Cl>[F:24][C:25]([F:32])([F:31])[C:26]([NH:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1)=[O:27]

Participants

5

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 21993671HCID 21993671, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of tert-butyl 4-aminopiperidine-1-carboxylate (48.7 g, 0.243 mol) and DIPEA (130 mL, 0.749 mol) in DCM (250 mL) was added ethyl trifluoroacetate (35.6 mL, 0.300 mol) dropwise while stirring. After 20 hours, the solution was washed with citric acid solution (200 mL×3, 10% w/v aq) and sodium bicarbonate solution (200 mL×3, cone aq), dried (MgSO4), and filtered through silica (24 g). The silica was washed with DCM and the combined eluant was partially concentrated (100 mL), and used directly in the next step.

Workup

  1. washthe solution was washed with citric acid solution (200 mL×3, 10% w/v aq) and sodium bicarbonate solution (200 mL×3, cone aq)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered through silica (24 g)
  4. washThe silica was washed with DCM
  5. concentrationthe combined eluant was partially concentrated (100 mL)

Sources & evidence

ORD record
ord-21e337a5af0f421a8f78884091dd22d3
Source dataset
uspto-grants-2014_07
Patent number
US08779128B2

Reaction notes

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