تفاعل #8174

معادلة التفاعل

NaH

11E

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

diphenylphosphinylhydroxylamine

→

compound 11F

المردود 15.4%

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

المردود 15.4%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction was cooled to rt
2. 2
   workup.ADDITION23, 3835-6 (1982)) was added
3. 3
   أخرىquenched by addition of water (3 mL)
4. 4
   استخلاصextracted with EtOAc (2×20 mL)
5. 5
   غسيلThe combined organics were washed with H2O (25 mL)
6. 6
   تجفيفdried over Na2SO4
7. 7
   تركيزconcentrated under reduced pressure
8. 8
   أخرىPurification by flash chromatography on silica gel eluting with 10% EtOAc/CH2Cl2

الإجراء التجريبي

NaH (60% in mineral oil, 7.9 mg, 0.20 mmol, 1.4 eq) was added to the solution of 11E (50 mg, 0.14 mmol, 1 eq) in DMF (3 mL). The reaction mixture was heated at 70° C. for 2 h. The reaction was cooled to rt and diphenylphosphinylhydroxylamine (52 mg, 0.22 mmol, 1.6 eq, made according to the procedure of Colvin, E. W. et. al. Tetrahedron Lett. 23, 3835-6 (1982)) was added. The reaction mixture was stirred at rt overnight and quenched by addition of water (3 mL) and extracted with EtOAc (2×20 mL). The combined organics were washed with H2O (25 mL), dried over Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography on silica gel eluting with 10% EtOAc/CH2Cl2 gave 8.0 mg (0.022 mmol, 15.4%) of compound 11F as a yellow solid. HPLC conditions: 93% at 3.54 min (YMC S5 ODS 4.6×50 mm, 10%-90% aqueous methanol over 4 minute gradient with 0.2% H3PO4, detecting at 220 nm).

المصدر