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Chemical Structure| 146603-99-8 Chemical Structure| 146603-99-8

Structure of 146603-99-8

Chemical Structure| 146603-99-8

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Product Details of [ 146603-99-8 ]

CAS No. :146603-99-8
Formula : C16H27NO4
M.W : 297.39
SMILES Code : O=C(N1CCC(C(OCC)=O)(CC=C)CC1)OC(C)(C)C
MDL No. :MFCD09265071
InChI Key :FOOVEGXEARQUBR-UHFFFAOYSA-N
Pubchem ID :16218270

Safety of [ 146603-99-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of [ 146603-99-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 146603-99-8 ]

[ 146603-99-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 72287-26-4 ]
  • potassium phosphate [ No CAS ]
  • [ 426842-84-4 ]
  • [ 280-64-8 ]
  • [ 146603-99-8 ]
  • ethyl 4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; ethyl acetate; Ethyl 4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylate 1.4 g of ethyl 4-allyl-1-(tert-butyloxy-carbonyl)piperidine-4-carboxylate were cooled to a temperature in the region of -30° C. and 11 cm3 of a 0.5 M solution of 9-borabicyclo[3.3.1]nonane in tetrahydrofuran were added, with stirring and under an inert atmosphere. After the addition, the temperature of the mixture was returned to about 20° C. The solution obtained was stirred for a further 4 hours, followed by addition of 0.09 g of palladium diphenylphosphinoferrocene chloride, 1.4 g of 4-iodo-3-fluoro-6-methoxyquinoline and 2.5 g of tribasic potassium phosphate. After stirring for 16 hours at a temperature in the region of 60° C., the reaction mixture was cooled to about 20° C. and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue obtained was taken up in ethyl acetate and water, the phases were separated by settling and the organic phase was dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue obtained was purified by chromatography, under atmospheric pressure, on a column of silica gel (particle size 70-200 mu; diameter 4.5 cm; mass 125 g), eluding with a mixture of dichloromethane/ethyl acetate (98/2 by volume), and collecting 20-cm3 fractions. Fractions 98 to 170 were combined and then concentrated to dryness under the above conditions. 1.5 g of ethyl 4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylate were obtained in the form of a thick brown oil. 1H NMR Spectrum (300 MHz, (CD3)2SO-d6, 6 in ppm): 1.02 (t, J=7 Hz: 3H); 1.30 (mt:2H); 1.39 (s: 9H); from 1.45 to 1.70 (mt: 4H); 1.92 (broad d, J=13.5 Hz: 2H); 2.81 (mt: 2H); 3.05 (broad t, J=6.5 Hz: 2H); 3.69 (broad d, J=13.5 Hz: 2H); 3.95 (s: 3H); 4.00 (q, J=7 Hz: 2H); 7.34 (d, J=2.5 Hz: 1H); 7.40 (dd, J=9 and 2.5 Hz: 1H); 7.97 (d, J=9 Hz: 1H); 8.70 (d, J=1 Hz: 1H).
  • 2
  • [ 72287-26-4 ]
  • potassium phosphate [ No CAS ]
  • [ 280-64-8 ]
  • [ 213772-63-5 ]
  • [ 146603-99-8 ]
  • ethyl 4-[3-(3-fluoroquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; diethyl ether; Ethyl 4-[3-(3-fluoroquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)piperidine-4-carboxylate 17.7 g of ethyl 4-allyl-1-(tert-butyloxy-carbonyl)piperidine-4-carboxylate in 200 cm3 of tetrahydrofuran were cooled to a temperature in the region of -30° C. and 135 cm3 of a 0.5M solution of 9-borabicyclo-[3.3.1]nonane in tetrahydrofuran were added with stirring and under an inert atmosphere. After the addition, the temperature of the mixture was returned to about 20° C. and the mixture was stirred for 2 hours. 14.8 g of 3-fluoro-4-iodoquinoline in 430 cm3 of tetrahydrofuran, 1.3 g of palladium diphenylphosphinoferrocene chloride and 29.8 g of tribasic potassium phosphate were added. The reaction mixture was then heated at a temperature in the region of 70° C. for 20 hours. After cooling to a temperature in the region of 20° C., the reaction mass was filtered and washed with 3 times 100 cm3 of tetrahydrofuran. The filtrate was concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The evaporation residue was taken up in 500 cm3 of diethyl ether, the insoluble material was washed with 3 times 100 cm3 of diethyl ether and the filtrate was concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The oil obtained was purified by chromatography under atmospheric pressure, on a column of silica gel (particle size 20-45 mu; diameter 6 cm; height 45 cm), eluding with a dichloromethane/ethyl acetate mixture (90/10 by volume) and collecting 120-cm3 fractions. Fractions 30 to 76 were combined and then concentrated to dryness under the same conditions as above. 13.7 g of ethyl 4-[3-(3-fluoroquinolin-4-yl)propyl]-1-(tert-butyloxycarbonyl)-piperidine-4-carboxylate were obtained in the form of a viscous orange-colored oil. Mass spectrum: EI m/z=444 M+. m/z=388 [M-tBu]+.m/z=343 [M-BOC]+m/z=288 C17H19FNO2+. m/z=184 C10H18NO2+.m/z=161 C10H8FN+m/z=57 C4H9+
 

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Technical Information

Categories

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[ 146603-99-8 ]

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Related Parent Nucleus of
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