Trifluoroacetic acid → Ethyl 3-fluoro-4-piperidineacetate

HRID 354520Notes

Reaction equation

HRID 354520 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:10]([F:20])[CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:20][CH:10]1[CH:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:12][CH2:13][NH:8][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23512083HCID 23512083, compound

Product 1

HCID 23511873Ethyl 3-fluoro-4-piperidineacetateYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 1-tert-butoxycarbonyl-3-fluoro-4piperidinylacetate (653 mg, 2.26 mmol) in CH2Cl2 (10 mL) was added TFA (5 mL) at 0° C. After being stirred at room temperature for 4 hr, the reaction mixture was concentrated. The residue was taken up with sat. NaHCO3 solution and extracted with THF—EtOAc (1:1, v/v). The extracts were dried over MgSO4 and concentrated to afford ethyl 3-fluoro-4-piperidinylacetate (420 mg, 98%) as a yellow oil. 1H-NMR (CDCl3) δ1.26 (t, J=7.4 Hz, 3H), 1.68-1.80 (m, 2H), 2.18 (m, 1H), 2.32 (dd, J=16.66, 6.8 Hz, 1H), 2.54 (dd, J=16.6, 7.5 Hz, 1H), 2.82 (m, 1H), 2.90, 3.00 (each d, J=14.4 Hz, total 1H), 3.31 (m, 1H), 3.51 (m, 1H), 4.15 (q, J=7.4 Hz, 2H), 4.82, 4.71 (each broad s, total 1H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. extractionextracted with THF—EtOAc (1:1
  3. dry with materialThe extracts were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-67cc669e409940899f3ccfaf51d0b52d
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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