m-Chloroperbenzoic acid → HCID 86680023, compound

HRID 521944Notes

Reaction equation

HRID 521944 reaction equation
[F:1][C:2]1([C:9]2[N:13]([CH3:14])[N:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[CH2:8][CH2:7][CH:6]=[CH:5][CH2:4][CH2:3]1.ClC1C=C(C=CC=1)C(OO)=[O:23]>C(Cl)Cl>[F:1][C:2]1([C:9]2[N:13]([CH3:14])[N:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[CH2:3][CH2:4][CH:5]2[CH:6]([O:23]2)[CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86713000HCID 86713000, compound

Product 1

HCID 86680023HCID 86680023, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (Z)-5-(1-fluorocyclohept-4-enyl)-1-methyl-4-nitro-1H-pyrazole (900 mg, 3.77 mmol) in DCM (30 mL) at 0° C. was added portionwise meta-chloroperoxybenzoic acid (1.0 g, 4.14 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 90 min before being quenched with a saturated solution of sodium hydrogencarbonate (30 mL). The mixture was extracted with DCM (100 mL), washed with aqueous 2 M NaOH (2×50 mL) and brine (30 mL). The organic layer was separated, dried over MgSO4 and concentrated under reduced pressure to give 5-(4-fluoro-8-oxabicyclo[5.1.0]octan-4-yl)-1-methyl-4-nitro-1H-pyrazole as a colourless solid (982 mg, quantitative) as a 2:5 ratio of diastereomers.

Workup

  1. custombefore being quenched with a saturated solution of sodium hydrogencarbonate (30 mL)
  2. extractionThe mixture was extracted with DCM (100 mL)
  3. washwashed with aqueous 2 M NaOH (2×50 mL) and brine (30 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-02de144e92924f4688b4ccd5a14ed590
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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