反应 #974991

反应方程式

ethyl 9-(2-aminoethyl)-2-methyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridine-1-carboxylate

diisobutylaluminum hydride toluene

triethylamine

acetic anhydride

Sodium sulfate decahydrate

→

title compound

收率 34.5%

N-[2-(1,2-dimethyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridin-9-yl)ethyl]acetamide

收率 34.5%

溶剂

tetrahydrofuran

Water

tetrahydrofuran

反应条件

后处理

1. 1
   过滤the mixture was filtered through celite
2. 2
   浓缩The filtrate was concentrated under reduced pressure
3. 3
   温度cooling
4. 4
   workup.STIRRINGthe mixture was stirred at room temperature for 30 min
5. 5
   其他the solvent was evaporated under reduced pressure
6. 6
   其他The residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→10/90) and recrystallization (ethyl acetate/diisopropyl ether)

实验过程

To a solution of ethyl 9-(2-aminoethyl)-2-methyl-8,9-dihydro-7H-cyclopenta[c]pyrazolo[1,5-a]pyridine-1-carboxylate (75.0 mg, 0.261 mmol) in tetrahydrofuran (2.6 mL) was added 1.5M diisobutylaluminum hydride toluene solution (2.1 mL, 3.2 mmol) at room temperature, and the mixture was stirred for 3 hr. Sodium sulfate decahydrate (2.1 g) was added and the mixture was filtered through celite. The filtrate was concentrated under reduced pressure. To a mixture of the residue and triethylamine (54.6 μL, 0.392 mmol) in tetrahydrofuran (2.5 mL) was added acetic anhydride (37.0 μL, 0.391 mmol) under ice-cooling, and the mixture was stirred at room temperature for 30 min. Water (70 μL) was added, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→10/90) and recrystallization (ethyl acetate/diisopropyl ether) to give the title compound (24.4 mg, yield 34%).

来源