N-Fluorobenzenesulfonimide → HCID 59739630, compound

HRID 1192949Notes

Reaction equation

HRID 1192949 reaction equation
[CH3:1][C:2]1([CH3:22])[O:6][N:5]=[C:4]([S:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][C:18]([F:21])([F:20])[F:19])(=[O:9])=[O:8])[CH2:3]1.C(N1CCN2CCN(CC(C)C)P1N(CC(C)C)CC2)C(C)C.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:56])(=O)=O)=CC=1>C(#N)C>[F:56][CH:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][C:18]([F:21])([F:19])[F:20])[S:7]([C:4]1[CH2:3][C:2]([CH3:22])([CH3:1])[O:6][N:5]=1)(=[O:8])=[O:9]

Participants

5

Reactant 3

HCID 588007N-FluorobenzenesulfonimideHCID 45712432,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo(3.3.3)undecaneHCID 59739548HCID 59739548, compound

Product 1

HCID 59739630HCID 59739630, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5,5-Dimethyl-3-(2-trifluoromethoxy-phenylmethanesulfonyl)-4,5-dihydroisoxazole (0.2 g, 0.59 mmol) was dissolved in acetonitrile (5 ml) and 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (Verkade's base) (0.44 ml, 1.24 mmol) was added dropwise at room temperature. After 5 minutes N-fluorobenzene-sulfonimide (NFSI) (393 mg, 1.24 mmol) was added in one portion. After 10 minutes the reaction was quenched by addition of water (10 ml). The mixture was acidified by addition of aqueous hydrochloric acid (2M) and extracted several times with ethyl acetate (3×10 ml). The combined organic phases were washed with saturated aqueous sodium hydrogencarbonate solution and with water, dried over magnesium sulfate and concentrated. The crude product was purified by chromatography on silica gel (eluent: ethyl acetate/hexane) to give the product (Compound No. 1.68 of Table 27) as colourless oil (145 mg, 69% yield).

Workup

  1. customAfter 10 minutes the reaction was quenched by addition of water (10 ml)
  2. additionThe mixture was acidified by addition of aqueous hydrochloric acid (2M)
  3. extractionextracted several times with ethyl acetate (3×10 ml)
  4. washThe combined organic phases were washed with saturated aqueous sodium hydrogencarbonate solution and with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by chromatography on silica gel (eluent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-359d97b1b10c4056b9b3cf359097c31b
Source dataset
uspto-grants-2014_03
Patent number
US08680290B2

Reaction notes

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