Ethyl trifluoroacetate → HCID 21993671, compound

HRID 1751780Notes

Reaction equation

HRID 1751780 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, conc 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. APCI/MS calcd. for C12H19F3N2O3 296.1. found m/z=294.9 (M−1).

Workup

  1. washthe solution was washed with citric acid solution (200 mL×3, 10% w/v aq) and sodium bicarbonate solution (200 mL×3, conc 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-4b0bf2dbd7c047708fb7576db0af1446
Source dataset
uspto-grants-2015_10
Patent number
US09161948B2

Reaction notes

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