Potassium Carbonate → HCID 86710213, compound

HRID 2168223Notes

Reaction equation

HRID 2168223 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][NH:3]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:14][CH2:15][O:16][C:17]1[CH:18]=[C:19]([CH:25]=[CH:26][CH:27]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(#N)C>[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:14][CH2:15][O:16][C:17]1[CH:18]=[C:19]([CH:25]=[CH:26][CH:27]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 641544(R)-2-MethylpyrrolidineHCID 54408639Ethyl 3-(2-bromoethoxy)benzoate

Product 1

HCID 86710213HCID 86710213, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of (2R)-2-methylpyrrolidine (300 mg, 3.52 mmol) and potassium carbonate (974 mg, 7.05 mmol) in Acetonitrile (20 mL) stirred at room temperature was added ethyl 3-[(2-bromoethyl)oxy]benzoate D46 (962 mg). The reaction mixture was stirred at 80° C. for 24 hours. After cooled to room temperature the mixture was filtrated and the filtrate was concentrated. The crude product was added to a silica gel column and was eluted with Hexane/EtOAc/TEA in ratio 50/50/0.5. The relevant fractions were isolated and solvent evaporated to afford the title compound D50 in 900 mg as a yellow oil. LCMS Retention time=1.09 mins, [M+H]+278 (5 min run)

Workup

  1. stirringThe reaction mixture was stirred at 80° C. for 24 hours
  2. temperatureAfter cooled to room temperature the mixture
  3. filtrationwas filtrated
  4. concentrationthe filtrate was concentrated
  5. additionThe crude product was added to a silica gel column
  6. washwas eluted with Hexane/EtOAc/TEA in ratio 50/50/0.5
  7. customThe relevant fractions were isolated
  8. customsolvent evaporated

Sources & evidence

ORD record
ord-8c2abe8e89f8431e83a4ac8c2ea2ae32
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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