Nitrogen → HCID 21963156, compound

HRID 2211821Notes

Reaction equation

HRID 2211821 reaction equation
N#N.[F:3][C:4]([F:18])([F:17])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])=[CH:7][CH:6]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].C1(S(N2C(C3C=CC=CC=3)O2)(=O)=[O:36])C=CC=CC=1>O1CCCC1>[OH:36][CH:13]1[CH2:14][CH2:15][N:11]([C:8]2[CH:7]=[CH:6][C:5]([C:4]([F:3])([F:17])[F:18])=[CH:10][CH:9]=2)[C:12]1=[O:16]

Participants

6

Reactant 4

HCID 947NitrogenHCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 12681871-[4-(Trifluoromethyl)phenyl]pyrrolidin-2-oneHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 21963156HCID 21963156, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

(Referring to Scheme 1) To a 100 mL round-bottomed flask equipped with septum and N2 inlet were added 600 mg (2.62 mmol) 1-(4-trifluoromethyl-phenyl)-pyrrolidin-2-one and 25 mL dry tetrahydrofuran. The solution was cooled to −78° C., and 5.24 mL (5.24 mmol) of a 1 M solution of lithium hexamethyldisilazide in tetrahydrofuran was added, and the reaction was stirred at −78° C. for 45 minutes. Then a solution of 856 mg (3.27 mmol) of N-(benzenesulfonyl)phenyloxaziridine in 5 mL dry tetrahydrofuran was added, and the reaction allowed to warm to room temperature and stirred overnight. The reaction was quenched with aqueous ammonium chloride solution and diluted with ethyl acetate, and the layers were separated. The aqueous phase was extracted three times with ethyl acetate, and the combined organic phase dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel with hexane/ethyl acetate to afford 241 mg (38%) of a while solid.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. customThe reaction was quenched with aqueous ammonium chloride solution
  4. additiondiluted with ethyl acetate
  5. customthe layers were separated
  6. extractionThe aqueous phase was extracted three times with ethyl acetate
  7. dry with materialthe combined organic phase dried over magnesium sulfate
  8. customevaporated
  9. customThe residue was chromatographed on silica gel with hexane/ethyl acetate
  10. customto afford 241 mg (38%) of a while solid

Sources & evidence

ORD record
ord-23934c8fc5ad4d5b8e3b1e928bbd8c21
Source dataset
uspto-grants-2006_09
Patent number
US07101885B2

Reaction notes

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