m-Chloroperbenzoic acid → 3-Oxa-tricyclo[3.2.2.02,4] nonane-2-carboxylic acid (4-nitro-3-trifluoromethyl-phenyl)-amide
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
Product 1
Reagents, catalysts & solvents 1
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). F. 3-Oxa-tricyclo[3.2.2.02,4]nonane-2-carboxylic acid N-(4-nitro-3-trifluoromethyl-phenyl)-hydrazide (11F)
Workup
- washThe organic solution was washed with sat. NaHCO3 (1×50 mL), brine (1×50 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
- customPurification by flash chromatography on silica gel eluting with 80% CH2Cl2/hexane
Sources & evidence
- ORD record
- ord-2975d623528d4c1983bcf37f33b4b1fc
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07087636B2
Reaction notes
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