m-Chloroperbenzoic acid → 3-Oxa-tricyclo[3.2.2.02,4] nonane-2-carboxylic acid (4-nitro-3-trifluoromethyl-phenyl)-amide

HRID 1591702Notes

Reaction equation

HRID 1591702 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]2[CH:25]3[CH2:31][CH2:30][CH:28]([CH:29]=2)[CH2:27][CH2:26]3)=[O:23])=[CH:17][C:16]=1[C:32]([F:35])([F:34])[F:33])([O-:14])=[O:13]>C(Cl)Cl>[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]23[O:9][CH:29]2[CH:28]2[CH2:27][CH2:26][CH:25]3[CH2:31][CH2:30]2)=[O:23])=[CH:17][C:16]=1[C:32]([F:33])([F:34])[F:35])([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 23546193Bicyclo[2.2.2]oct-2-ene-2-carboxylic acid (4-nitro-3-trifluoromethyl-phenyl)-amide

Product 1

HCID 235461863-Oxa-tricyclo[3.2.2.02,4] nonane-2-carboxylic acid (4-nitro-3-trifluoromethyl-phenyl)-amideYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

mCPBA (60% mixture, 518 mg, 3.00 mmol, 3 eq) was added to a solution of 11D (340 mg, 1.0 mmol, 1.0 eq) in CH2Cl2 (20 mL). The reaction mixture was stirred at rt overnight and then diluted with CH2Cl2 (40 mL). The organic solution was washed with sat. NaHCO3 (1×50 mL), brine (1×50 mL), dried over Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography on silica gel eluting with 80% CH2Cl2/hexane gave 205 mg (0.58 mmol, 57.6%) of compound 11E. HPLC conditions: 95% at 3.70 min (YMC S5 ODS 4.6×50 mm, 10%-90% aqueous methanol over 4 minute gradient with 0.2% H3PO4, detecting at 220 nm).

Workup

  1. washThe organic solution was washed with sat. NaHCO3 (1×50 mL), brine (1×50 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customPurification by flash chromatography on silica gel eluting with 80% CH2Cl2/hexane

Sources & evidence

ORD record
ord-45c287c476ca4d51acbb47c9ea183b78
Source dataset
uspto-grants-2007_11
Patent number
US07291637B2

Reaction notes

Loading…