反应详情

To a solution of KOH (0.024 g, 0.36 mmol) in CH3CN (20 ml) at the reflux temp. was added 2-(2-ethyl-4-formylphenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane (Method D11a; 0.127 g, 0.36 mmol). The reaction mixture was heated at the reflux temp. for 4 h, cooled to room temp., and concentrated under reduced pressure The residue was diluted with water (15 mL) and extracted with CH2Cl2 (3×15 mL). The combined organic layers were washed with a saturated NaCl solution and dried (Na2SO4). The resulting material was purified by preparative TLC (30% EtOAc/hex) to give 2-(2-ethyl-4-(2-cyanovinyl)phenylimino)-1-cyclopentyl-3-thia-1-azaspiro[4.4]nonane as 1:3 cis/trans mixture of isomers (0.050 g): TLC (30% EtOAc/hex) Rf0.56.

1. temperatureThe reaction mixture was heated at the reflux temp
2. temperaturecooled to room temp.
3. concentrationconcentrated under reduced pressure The residue
4. additionwas diluted with water (15 mL)
5. extractionextracted with CH2Cl2 (3×15 mL)
6. washThe combined organic layers were washed with a saturated NaCl solution
7. dry with materialdried (Na2SO4)
8. customThe resulting material was purified by preparative TLC (30% EtOAc/hex)