تفاعل #8173

معادلة التفاعل

mCPBA

11D

Bicyclo[2.2.2]oct-2-ene-2-carboxylic acid (4-nitro-3-trifluoromethylphenyl)-amide

→

compound 11E

المردود 58.0%

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

المردود 58.0%

المذيبات

CH2Cl2

CH2Cl2

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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)

المصدر