Potassium Carbonate → HCID 69003415, compound

HRID 2103324Notes

Reaction equation

HRID 2103324 reaction equation
[O:1]([C:8]1[CH:19]=[CH:18][C:11]([O:12][C@@H:13]2[CH2:17][CH2:16][NH:15][CH2:14]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][O:21][C:22](=[O:27])[CH2:23][CH2:24][CH2:25]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:20][O:21][C:22](=[O:27])[CH2:23][CH2:24][CH2:25][N:15]1[CH2:16][CH2:17][C@@H:13]([O:12][C:11]2[CH:18]=[CH:19][C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:9][CH:10]=2)[CH2:14]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 107604Methyl 4-bromobutyrateHCID 26192134HCID 26192134, compound

Product 1

HCID 69003415HCID 69003415, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

(R)-3-(4-Phenoxy-phenoxy)-pyrrolidine (1.24 g, 4.25 mmol) was taken into anhydrous DMF (10 mL) in a nitrogen flushed 100 mL, 1-neck round bottom flask. Methyl-4-bromobutyrate (846 mg, 4.68 mmol) was added to the mixture followed by potassium carbonate (1.18 g, 8.5 mmol). The reaction was heated at 60° C. for 24 h. The mixture was then cooled to room temperature and partitioned between ethyl acetate and water. The water layer was washed with ethyl acetate (3×). The combined ethyl acetate layers were then washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to dryness. The resulting residue was then purified by silica gel flash chromatography (20:1 silica ratio, eluted with 1:1 ethyl acetate and hexane) to obtain the title product (894.4 mg, 59%) LCMS; m/z 356 (M+1); 1H NMR (400 MHz, DMSO) δ 1.65-1.78 (m, 3H), 2.21-2.26 (m, 1H), 2.32-2.35 (m, 2H), 2.37-2.42 (m, 3H), 2.58-2.61 (m, 1H), 2.63-2.69 (m, 1H), 2.80-2.84 (m, 1H), 3.58 (s, 3H), 4.80 (s, 1H), 6.89-6.98 (m, 6H), 7.07-7.09 (m, 1H), 7.32-7.36 (m, 2H).

Workup

  1. customflushed 100 mL, 1-neck round bottom flask
  2. temperatureThe mixture was then cooled to room temperature
  3. custompartitioned between ethyl acetate and water
  4. washThe water layer was washed with ethyl acetate (3×)
  5. washThe combined ethyl acetate layers were then washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe resulting residue was then purified by silica gel flash chromatography (20:1 silica ratio, eluted with 1:1 ethyl acetate and hexane)

Sources & evidence

ORD record
ord-6df82a4a6b3442f6bf28ca64010bd2cc
Source dataset
uspto-grants-2009_08
Patent number
US07576102B2

Reaction notes

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