Hydrochloric Acid → HCID 21990164, compound

HRID 1092769Notes

Reaction equation

HRID 1092769 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:13][C:14]([OH:16])=O)=[CH:9][C:4]=2[CH:3]=[CH:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:29]1[CH2:33][CH2:32][CH:31]([OH:34])[CH2:30]1.Cl>O1CCCC1.C(OCC)(=O)C.O.C(N(CC)CC)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][O:12][CH2:13][C:14]([N:29]3[CH2:33][CH2:32][CH:31]([OH:34])[CH2:30]3)=[O:16])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 982104-HydroxypyrrolidineHCID 21990176HCID 21990176, compound

Product 1

HCID 21990164HCID 21990164, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

In 13.0 mL of tetrahydrofuran was dissolved 1.28 g of 2-[2-(1-benzofuran-5-yl)ethoxy]acetic acid and the solution was cooled to 5° C., after which 1.41 g of 1,1′-carbonyldiimidazole was added thereto and the resulting mixture was stirred at room temperature for 2 hours. To the reaction mixture were added 1.22 mL of triethylamine and 0.72 mL of 3-pyrrolidinol, followed by stirring at room temperature for 2 hours. Water and ethyl acetate were added to the reaction mixture and the pH was adjusted to 1 with 6 mol/L hydrochloric acid, after which the organic layer was separated. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and then a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure to obtain 1.39 g of 2-[2-(1-benzofuran-5-yl)ethoxy]-1-(3-hydroxy-1-pyrrolidinyl)-1-ethanone as a colorless oil.

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. customafter which the organic layer was separated
  3. washThe organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution
  4. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  5. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-68066306af9b4a24b5e7a43a7b646c5e
Source dataset
uspto-grants-2012_03
Patent number
US08129535B2

Reaction notes

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