反应详情

To a flask was added 0.10 g (0.34 mmol) of N-mesityl-7-nitro-1,3-benzoxazol-2-amine and 40 ml of methanol. The flask was purged with nitrogen followed by the addition of 0.01 g of 10% palladium on carbon. The flask was evacuated and pressurized to 2-3 psig hydrogen and stirred for 1 h. After completion as determined by HPLC, the reaction was filtered through GF/F filter paper. The filtrate was transferred to round bottom flask and 0.1 ml (1.7 mmol) of propionaldehyde, 0.1 g (1.7 mmol) of NaBH3CN and 1 ml of acetic acid were added. The mixture was stirred overnight, then diluted with ethyl acetate and washed with water. The organic phase was dried over magnesium sulfate. Filtration, removal of solvent and purification of the residue via Biotage chromatography eluting with 5% methanol/dichloromethane gave 0.11 g (90% for 2 steps) of product.

1. customThe flask was purged with nitrogen
2. additionfollowed by the addition of 0.01 g of 10% palladium on carbon
3. customThe flask was evacuated
4. filtrationthe reaction was filtered through GF/F
5. filtrationfilter paper
6. customThe filtrate was transferred to round bottom flask
7. stirringThe mixture was stirred overnight
8. washwashed with water
9. dry with materialThe organic phase was dried over magnesium sulfate
10. filtrationFiltration, removal of solvent and purification of the residue via Biotage chromatography
11. washeluting with 5% methanol/dichloromethane
12. customgave 0.11 g (90% for 2 steps) of product