反应详情

The crude (3R)-1′-(anthracene-9-carbonyl)-[1,4′]bipiperidinyl-3-carboxylic acid as prepared above (approx 22 mmol) was heated under reflux in a mixture of chloroform (75 mL, Aldrich, amylenes-stabilized) and thionyl chloride (10 mL, 0.137 mmol) until all the solid had dissolved. The mixture was diluted with toluene, evaporated to dryness under vacuum and anhydrous dichloromethane (40 mL) added. A mixture of morpholine (21 mmol, 1.81 mL) and triethylamine (62 mmol, 8.7 mL) in anhydrous dichloromethane (40 mL) was added and the solution was stirred for 16 hr at ambient temperature. The mixture was washed with ice-cold 0.1M sodium hydroxide solution, dried over anhydrous sodium sulfate, diluted with toluene and evaporated to dryness. The residue was purified by chromatography on 240 g silica gel eluting with a 4%-7%-10% methanol-dichloromethane gradient to give the title compound as a pale yellow glassy foam.

1. temperaturewas heated
2. dissolutionhad dissolved
3. customevaporated to dryness under vacuum and anhydrous dichloromethane (40 mL)
4. additionadded
5. additionwas added
6. washThe mixture was washed with ice-cold 0.1M sodium hydroxide solution
7. dry with materialdried over anhydrous sodium sulfate
8. additiondiluted with toluene
9. customevaporated to dryness
10. customThe residue was purified by chromatography on 240 g silica gel eluting with a 4%-7%-10% methanol-dichloromethane gradient