Pyrrolidine → HCID 69451115, compound

HRID 2229550Notes

Reaction equation

HRID 2229550 reaction equation
[CH2:1]([O:3][C:4](=[O:29])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13]CC=C)=[CH:9][C:8]=1[C:17](=[O:28])[NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:21]=1[F:27])[CH3:2].O1CCOCC1.N1CCCC1>C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:29])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[C:17](=[O:28])[NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:21]=1[F:27])[CH3:2]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 312751,4-DioxaneHCID 69451845HCID 69451845, compound

Product 1

HCID 69451115HCID 69451115, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of [4-allyloxy-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid ethyl ester (1.02 g, 2.40 mmol) and Pd(Ph3)4 (15 mg, 1.4 mol %) in a aq 1,4-dioxane solution (10 mL, 95% 1,4-dioxane) was treated with pyrrolidine (0.45 mL, 5.39 mmol) in a dropwise manner. After stirring for 2 h at room temperature, the solution was diluted with ethyl acetate and washed with aq 10% HCl, sat's aq NaCl, dried over Na2SO4, filtered and concentrated. The resulting crude solid was recrystallized with ethyl acetate and heptane to give [4-hydroxy-2-(4-bromo-2-fluoro-benzylcarbamoyl)-phenoxy]-acetic acid ethyl ester (0.780 g, 76%) as a white crystalline solid.

Workup

  1. washwashed with aq 10% HCl
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting crude solid was recrystallized with ethyl acetate and heptane

Sources & evidence

ORD record
ord-a125c5aec6cd4c4a89576ed51db9828c
Source dataset
uspto-grants-2002_07
Patent number
US06420426B1

Reaction notes

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