Oxygen → HCID 21971269, compound

HRID 1954591Notes

Reaction equation

HRID 1954591 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH2:13]([O:15][C:16]([C:18]1([C@H:21]2[CH2:25][N:24]([C@H:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH3:27])[C:23](=[O:34])[CH2:22]2)[CH2:20][CH2:19]1)=[O:17])[CH3:14].[O:35]=O.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH2:13]([O:15][C:16]([C:18]1([C@H:21]2[CH2:25][N:24]([C@H:26]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH3:27])[C:23](=[O:34])[C@@H:22]2[OH:35])[CH2:19][CH2:20]1)=[O:17])[CH3:14]

Participants

8

Reactant 5

HCID 977OxygenHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 11023011HCID 11023011, compoundHCID 178418339Butyllithium

Product 1

HCID 21971269HCID 21971269, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

Under a nitrogen atmosphere, diisopropylamine (3.93 ml, 28.0 mmol) was dissolved in anhydrous tetrahydrofuran (200 ml) to which, after cooling to -78° C., was subsequently added dropwise an n-hexane solution of 1.69 M n-butyl lithium (15.9 ml, 26.9 mmol) over a period of 10 minutes. After 20 minutes of stirring at 0° C. and subsequent cooling to -78° C., to the resulting reaction solution was added dropwise anhydrous tetrahydrofuran solution (40 ml) of 4-(S)-(1-ethoxycarbonylcyclopropyl)-1-[1-(S)-phenylethyl]-2-pyrrolidone (6.74 g, 22.4 mmol) over a period of 15 minutes. The reaction solution was stirred at -78° C. for 10 minutes and then the reaction vessel was charged with dried oxygen at the same temperature. The reaction solution was stirred at -78° C. for 20 minutes and then mixed-with a saturated ammonium chloride aqueous solution (200 ml). This was warmed up to room temperature and the organic layer was separated. The aqueous layer was extracted with diethyl ether (200 ml×2), and the organic layers were combined and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the resulting residue was subjected to flash silica gel chromatography and eluted with an eluant of n-hexane:ethyl acetate=2:1, to thereby obtain 5.21 g (73%) of the title compound as a colorless oil.

Workup

  1. temperaturesubsequent cooling to -78° C., to the resulting reaction solution
  2. stirringThe reaction solution was stirred at -78° C. for 10 minutes
  3. stirringThe reaction solution was stirred at -78° C. for 20 minutes
  4. temperatureThis was warmed up to room temperature
  5. customthe organic layer was separated
  6. extractionThe aqueous layer was extracted with diethyl ether (200 ml×2)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter filtration
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. washeluted with an eluant of n-hexane

Sources & evidence

ORD record
ord-2e52423b8a4240d4bd12d7a08dfa0622
Source dataset
uspto-grants-2000_09
Patent number
US06121285

Reaction notes

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