反应详情

A mixture of 20.2 g (0.1 mol) 6-hydroxy-naphthalene-2-carboxylic acid methyl ester (commercially available), 18.6 g (0.13 mol) 1-piperidinepropanol (commercially available), 50.4 g (0.2 mol) 1,1′-(azodicarbonyl)dipiperidine and 58 ml (0.2 mol) tri-n-butyl-phosphine in 400 ml THF was stirred at room temperature for 16 h. The suspension was filtered off and the filtrate evaoprated to dryness. The residue was taken up in 200 ml DCM and 400 g Isolute® HM-N (Argonaut Technologies Inc., support material for accelerated solvent extraction) was added and evaporated to dryness. The residue was chromatographed over silica eluting with a gradient formed from DCM/MeOH(2N NH3) 99/1 to 9/1. After evaporation the residue was treated with heptan/diethyl ether and the precipitate filtered of and washed again with heptan/diethyl ether. After drying under reduced pressure at 50° C. 25 g (76%) of the title compound was obtained as white solid. MS (m/e): 328.3 (MH+, 100%)

1. filtrationThe suspension was filtered off
2. extraction400 g Isolute® HM-N (Argonaut Technologies Inc., support material for accelerated solvent extraction)
3. additionwas added
4. customevaporated to dryness
5. customThe residue was chromatographed over silica eluting with a gradient
6. customformed from DCM/MeOH(2N NH3) 99/1 to 9/1
7. customAfter evaporation the residue
8. additionwas treated with heptan/diethyl ether
9. filtrationthe precipitate filtered of and
10. washwashed again with heptan/diethyl ether
11. customAfter drying under reduced pressure at 50° C