Novel pyrrolidine compound and application as melanocortin receptor agonist
A kind of technology of pyrrolidine and compound, applied in the field of novel pyrrolidine compound
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Embodiment 340
[1109] The starting material of Example 340 can be produced, for example, according to the above-mentioned scheme in the following manner.
[1110] By reducing the compound represented by the general formula [102] (in the formula [102], the symbol has the same meaning as above), the general formula [103] (in the formula [103], the symbol has the same meaning as above) can be obtained. Compounds represented by the same meaning).
[1111] The obtained compound [103] is converted, thus the general formula [104] (in the formula [104], X r1 represents a leaving group, and other symbols have the same meanings as above).
[1112] The obtained compound [104] is converted to obtain a compound represented by the general formula [105] (in the formula [105], the symbols have the same meanings as above).
[1113]The compound represented by the general formula [106] (in the formula [106], the symbols have the same meanings as above) can be obtained by subjecting the obtained compound [105...
Embodiment 1
[1209]
[1210] To the compound 1 (142mg) and compound 2 Acetic acid (20 μL) was added to a dichloromethane solution (26 μL) (2 mL), stirred at room temperature for 10 minutes, sodium triacetoxyborohydride (74 mg) was added, and stirred for 16 hours. After adding saturated aqueous sodium bicarbonate solution and water and stirring, it was extracted with dichloromethane. The obtained organic layer was washed with saturated brine, dried and concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=80:20~50:50) to obtain 1-[2-(1-{[(3R,4R) -3-fluoro-4-(4-methoxyphenyl)-1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-3-yl]carbonyl}piperidin-4-yl)-5 -(Trifluoromethyl)phenyl]piperidine-4-carboxylic acid ethyl ester 3 (154 mg). MS(ESI): m / z 690[M+H]+
Embodiment 2
[1212]
[1213] To the compound 1 (80mg) and compound 2 (528 μL) in dichloromethane (2 mL) were added acetic acid (76 μL) and sodium triacetoxyborohydride (336 mg), and stirred under reflux for 16 hours. After adding saturated aqueous sodium bicarbonate solution and water and stirring, it was extracted with dichloromethane. The obtained organic layer was washed with saturated brine, dried and concentrated under reduced pressure. The residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=95:5~70:30) to obtain 1-[2-(1-{[(3R,4R) -1-cyclopropyl-3-fluoro-4-(4-methoxyphenyl)pyrrolidin-3-yl]carbonyl}piperidin-4-yl)-5-(trifluoromethyl)phenyl] Ethyl piperidine-4-carboxylate 3 (29 mg). MS(APCI): m / z 646[M+H]+
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