反应详情

温度

5 °C

166 e) To a cooled solution of 2.0 M of lithium tetrahydroborate in tetrahydrofuran (13 mL, 26 mmol) at 5° C. was added dropwise a solution of 5-amino-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (1.0 g, 4.3 mmol) in tetrahydrofuran (50 mL). Gas evolution was noted. The mixture was stirred for 1 hour at 5° C. then warmed to room temperature and stirred for 24 hours. The mixture was cooled to 5° C. in a ice/water bath and the reaction was quenched by addition of sodium sulfate decahydrate (3 g). Gas evolution noted. The mixture was stirred for 2 hours at room temperature. The suspension was filtered through a plug of diatomaceous earth and rinsed with tetrahydrofuran. The filtrate was dried over magnesium sulfate, filtered and evaporated. The residue was purified via flash chromatography (silica gel column and 0%→20% methanol: dichloromethane). 2-Methyl-2,3-dihydro-1H-isoindol-5-ylamine was isolated as an orange solid (0.271 g, 43%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 6.82 (d, J=7.9 Hz, 1H), 6.41 (s, 1H), 6.37 (d, J=8.1 Hz, 1H), 4.86 (br s, 2H), 3.64 (s, 2H), 3.62 (s, 2H), 2.42 (s, 3H). MS=149 (MH)+.

1. temperaturethen warmed to room temperature
2. stirringstirred for 24 hours
3. temperatureThe mixture was cooled to 5° C. in a ice/water bath
4. customthe reaction was quenched by addition of sodium sulfate decahydrate (3 g)
5. stirringThe mixture was stirred for 2 hours at room temperature
6. filtrationThe suspension was filtered through a plug of diatomaceous earth
7. washrinsed with tetrahydrofuran
8. dry with materialThe filtrate was dried over magnesium sulfate
9. filtrationfiltered
10. customevaporated
11. customThe residue was purified via flash chromatography (silica gel column and 0%→20% methanol: dichloromethane)