反应详情

To a solution of diisopropylamine (0.15 g) in tetrahydrofuran (15 mL) was added n-butyllithium in hexane (0.75 mL, 2M solution) at -20° to -30° and the solution was stirred at -20° to -30° C. for 30 minutes. To the solution was added at -20° to -30° C. (in one portion) trans-1,3,4,4a,5,7,8,9,10,10a-decahydro-2-methyl-6H-cyclopenta[4,5]pyrrolo[2,3-g]isoquinolin-10(2H)-one (0.244 g) and the mixture was stirred at -20° C. for 2 hours. To the solution was added the crude 2,2-dimethyl-4-[(1-oxodecyl)oxy]butanoyl chloride (0.45 g) in tetrahydrofuran at -20° to -30° and the mixture was stirred at this temperature for an additional 1 hour. The mixture was poured onto ice water and extracted in the dichloromethane. The combined dichloromethane extracts were washed with brine dried sodium sulfate and evaporated. The crude product was chromatographed on silica gel eluting with 5% methanol in dichloromethane to give 0.24 g of oily material (47%), trans-1,3,4,4a,5,6,7,8,9,10a-Decahydro-6-[2,2-dimethyl-1-oxo-4-[(1-oxodecyl)oxy]butyl]-2-methylcyclopenta[4,5]pyrrolo[2,3-g]isoquinolin-10(2H)-one IR (CHCl3), 1778 (C=O) and 1657 (C=O); NMR (CDCl3), δ0.88 (t, 3, CH3); 1.2-1.4 (m, 20, CH2 and CH3) 2.41 (5, 3, CH3); 3.04 (br.d, 1, CH); 3.56 (br.d, 1, CH); 4.14 (t, 2, CH2); MS m/e 512 (M+).

1. stirringthe mixture was stirred at -20° C. for 2 hours
2. stirringthe mixture was stirred at this temperature for an additional 1 hour
3. additionThe mixture was poured onto ice water
4. extractionextracted in the dichloromethane
5. washThe combined dichloromethane extracts were washed with brine dried sodium sulfate
6. customevaporated
7. customThe crude product was chromatographed on silica gel eluting with 5% methanol in dichloromethane