反应详情

A mixture of 2,2′-Bis(diphenylphosphino)1,1′-binaphthyl[BINAP] (54.35 mg, 0.085 mmol) and Palladium(II)acetate[Pd(OAc)2] (6.95 mg, 0.028 mmol) in dry toluene (3 ml) was stirred vigorously and nitrogen was bubbled through the suspension for 30 minutes. To this, 1,4-Dioxa-8-aza-spiro[4.5]-decane (100 mg, 0.699 mmol), 3-Bromo-4-methyl-benzoic acid methyl ester (192.1 mg, 0.839 mmol) and dry Cesium Carbonate (683.5 mg, 2.09 mmol) was added. Nitrogen was bubbled through for another 30 minutes; the mixture was allowed to reflux overnight. The mixture was cooled, diluted with ethylacetate, water was added and the layers separated. The aqueous layer was extracted with ethyl acetate) and the two organic extracts were combined. The organics were washed with brine, then dried (sodium sulfate), filtered and concentrated. Further purification by silica gel chromatography using 5-10% ethyl acetate/Hexane as eluent provided 3-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-4-methyl-benzoic acid methyl ester [11] as a yellow solid [150.5 mg, 61.7%]

1. customnitrogen was bubbled through the suspension for 30 minutes
2. customNitrogen was bubbled through for another 30 minutes
3. temperatureto reflux overnight
4. temperatureThe mixture was cooled
5. additiondiluted with ethylacetate, water
6. additionwas added
7. customthe layers separated
8. extractionThe aqueous layer was extracted with ethyl acetate) and the two organic extracts
9. washThe organics were washed with brine
10. dry with materialdried (sodium sulfate)
11. filtrationfiltered
12. concentrationconcentrated
13. customFurther purification by silica gel chromatography