Ethyl bromoacetate → HCID 86630534, compound

HRID 2093148Notes

Reaction equation

HRID 2093148 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(N(CC)C(C)C)(C)C.Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]1[CH2:11][CH2:12][N:13]([CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 24904257HCID 24904257, compound

Product 1

HCID 86630534HCID 86630534, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-(2-fluoro-4-methoxyphenyl)piperidine (40 mg; 0.19 mmol) in DMF (1 mL) under an atmosphere of N2 was added N,N-diisopropylethylamine (33 μL; 0.19 mmol), followed by ethyl bromoacetate (21 μL; 0.19 mmol). The resultant solution was stirred at room temperature for 2.5 h. The reaction was partitioned between EtOAc (10 mL) and H2O (10 mL). The aqueous layer was extracted with EtOAc (3×10 mL) and the combined extracts were washed with brine (10 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash silica gel chromatography (0-25% EtOAc/hexanes gradient) to afford ethyl [4-(2-fluoro-4-methoxyphenyl)piperidin-1-yl]acetate as a colorless oil. LCMS=295.9 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.14 (t, J=8.7 Hz, 1 H), 6.65 (dd, J=8.5, 2.5 Hz, 1 H), 6.58 (dd, J=12.43, 2.5 Hz, 1 H), 4.20 (q, J=7.1 Hz, 2 H), 3.77 (s, 3 H), 3.26 (s, 2H), 3.06 (d, J=11.4 Hz, 2 H), 2.80 (tt, J=12.1, 3.7 Hz, 1 H), 2.32 (t, J=11.2 Hz, 2 H), 1.87 (qd, J=12.3, 3.3 Hz, 2 H), 1.78 (d, J=12.1 Hz, 2 H), 1.29 (t, J=7.1 Hz, 3 H).

Workup

  1. customThe reaction was partitioned between EtOAc (10 mL) and H2O (10 mL)
  2. extractionThe aqueous layer was extracted with EtOAc (3×10 mL)
  3. washthe combined extracts were washed with brine (10 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash silica gel chromatography (0-25% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-00557dab9f4444359f2ac49180222433
Source dataset
uspto-grants-2013_05
Patent number
US08440702B2

Reaction notes

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