Potassium Carbonate → HCID 68998463, compound

HRID 2103328Notes

Reaction equation

HRID 2103328 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:18]=[CH:17][C:10]([O:11][C@@H:12]3[CH2:16][CH2:15][NH:14][CH2:13]3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH3:21][O:22][C:23](=[O:28])[CH2:24][CH2:25][CH2:26]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:21][O:22][C:23](=[O:28])[CH2:24][CH2:25][CH2:26][N:14]1[CH2:15][CH2:16][C@@H:12]([O:11][C:10]2[CH:17]=[CH:18][C:7]([O:6][C:5]3[CH:19]=[CH:20][C:2]([Cl:1])=[CH:3][CH:4]=3)=[CH:8][CH:9]=2)[CH2:13]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 107604Methyl 4-bromobutyrateHCID 69000630HCID 69000630, compound

Product 1

HCID 68998463HCID 68998463, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

(R)-3-[4-(4-Chloro-phenoxy)-phenoxy]-pyrrolidine (344 mg, 1.05 mmol) was taken into anhydrous dimethylformamide (5 mL), and methyl-4-bromobutyrate (209 mg, 1.16 mmol), potassium carbonate (290 mg, 2.1 mmol) was added. The reaction was sealed and heated to 60° C. and left to react for 24 h. The mixture was then partitioned between ethyl acetate and water. The aqueous layer was washed with ethyl acetate 3×. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to dryness. The residue was purified by flash column chromatography (50:1 packing ration, eluted with 5% methanol in dichloromethane) to obtain the title product (86.8 mg, 21%); LCMS; m/z 390 (M) 71% pure; 1H NMR (400 MHz, DMSO); δ 1.66-1.80 (m, 3H), 2.22-2.26 (m, 1H), 2.31-2.35 (m, 2H), 2.37-2.41 (m, 3H), 2.58-2.67 (m, 2H), 2.81-2.84 (m, 1H), 3.58 (s, 3H), 4.80-4.83 (m, 1H), 6.91-6.95 (m, 4H), 6.98-7.00 (m, 2H), 7.37-7.39 (m, 2H).

Workup

  1. additionwas added
  2. customThe reaction was sealed
  3. waitleft
  4. customto react for 24 h
  5. customThe mixture was then partitioned between ethyl acetate and water
  6. washThe aqueous layer was washed with ethyl acetate 3×
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated to dryness
  10. customThe residue was purified by flash column chromatography (50:1 packing ration, eluted with 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-3cf0029cb7c54aa7b4d4c83b3e1f7faa
Source dataset
uspto-grants-2009_08
Patent number
US07576102B2

Reaction notes

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