Diisopropylamine → HCID 53923125, compound

Temperature

-78 °C

To a cooled solution of lithium diisopropylamide (generated from diisopropylamine (109 mg, 1.07 mmol) and a solution of n-butyllithium in hexanes (0.49 mL of a 2.5M solution, 1.22 mmol)) in THF (0.5 mL) at -78° C. was added 4-picoline (95 μL, 0.98 mmol). Stirred -78° to 0° C. for 1 h. The reaction mixture was cooled to -78° C. and a solution of 2,4-di-n-propyloxy-N-methoxy-N-methyl-benzamide from Step B (274 mg, 0.98 mmol) in THF (0.5 mL) was added dropwise. The reaction was stirred <0° C. for 4 h and then quenched by the addition of a saturated aqueous solution of ammonium chloride. The mixture was extracted with ethyl acetate (2 times). The combined extracts were successively washed with water and saturated salt solution and dried over anhydrous sodium sulfate. The solution was filtered and the solvents removed by rotoevaporation. The residue was purified by flash column chromatography on silica gel eluted with 0-50% ethyl acetate in hexanes to yield the title compound (147 mg, 48% yield), mass spectrum (CI) m/e=314 (M+1)+.

1. stirringThe reaction was stirred <0° C. for 4 h
2. customquenched by the addition of a saturated aqueous solution of ammonium chloride
3. extractionThe mixture was extracted with ethyl acetate (2 times)
4. washThe combined extracts were successively washed with water and saturated salt solution
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationThe solution was filtered
7. customthe solvents removed by rotoevaporation
8. customThe residue was purified by flash column chromatography on silica gel
9. washeluted with 0-50% ethyl acetate in hexanes

ORD record

ord-aa150002075b4e0e8f8975e30d982108

Source dataset

uspto-grants-1999_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05880139