Potassium Carbonate → HCID 86711700, compound

HRID 1855311Notes

Reaction equation

HRID 1855311 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:28]([O:30][C:31]([C@H:33]1[CH2:37][CH2:36][C:35](=[O:38])[NH:34]1)=[O:32])[CH3:29]>C(#N)C.[Cu]I.CNCCNC>[Si:15]([O:14][C@H:8]([C:5]1[CH:6]=[CH:7][C:2]([N:34]2[C:35](=[O:38])[CH2:36][CH2:37][C@@H:33]2[C:31]([O:30][CH2:28][CH3:29])=[O:32])=[CH:3][CH:4]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 643508ethyl (2R)-5-oxopyrrolidine-2-carboxylateHCID 11383144HCID 11383144, compound

Product 1

HCID 86711700HCID 86711700, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolvent2×HCID 8070N,N'-DimethylethylenediamineSolventHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Solvent

Conditions

Temperature
23 °C

Procedure

To a flask containing acetonitrile was added [(S)-1-(4-bromo-phenyl)-hexyloxy]-tert-butyl-dimethyl-silane and potassium carbonate. The solution mixture was heated to reflux for a period of time. The solution mixture was then cooled to ambient temperature (˜23° C.) before adding a solution of (R)-5-oxo-pyrrolidine-2-carboxylic acid ethyl ester in acetonitrile, CuI and N,N′-dimethylethylenediamine. The reaction mixture was heated to reflux until the ethyl ester was consumed. The reaction mixture was cooled to ambient temperature, filtered through a bed of Celite and rinsed forward with acetonitrile. The filtrate was washed twice with aqueous ammonium acetate and dried over sodium sulfate. The mixture was passed through a bed of silica, washed with MTBE, and concentrated under reduced pressure to give the product as a light yellow oil.

Workup

  1. temperatureThe solution mixture was heated
  2. temperatureto reflux for a period of time
  3. temperatureThe reaction mixture was heated
  4. customwas consumed
  5. temperatureThe reaction mixture was cooled to ambient temperature
  6. filtrationfiltered through a bed of Celite
  7. washrinsed forward with acetonitrile
  8. washThe filtrate was washed twice with aqueous ammonium acetate
  9. dry with materialdried over sodium sulfate
  10. washwashed with MTBE
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5f5a55ccd808439b918b0ecab5ef556b
Source dataset
uspto-grants-2015_02
Patent number
US08962863B2

Reaction notes

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