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Chemical Structure| 647863-25-0 Chemical Structure| 647863-25-0

Structure of 647863-25-0

Chemical Structure| 647863-25-0

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Product Details of [ 647863-25-0 ]

CAS No. :647863-25-0
Formula : C12H16F3NO4
M.W : 295.26
SMILES Code : CC(C)(C)OC(=O)N1CCC(C(=O)C(F)(F)F)C(=O)C1
English Name :tert-Butyl 3-oxo-4-(2,2,2-trifluoroacetyl)piperidine-1-carboxylate
MDL No. :MFCD23106426
InChI Key :FUHZEIWXMXDMSS-UHFFFAOYSA-N
Pubchem ID :18456551

Safety of [ 647863-25-0 ]

Application In Synthesis of [ 647863-25-0 ]

* 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 [ 647863-25-0 ]

[ 647863-25-0 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 647863-25-0 ]
  • [ 422-62-8 ]
  • [ 911636-91-4 ]
YieldReaction ConditionsOperation in experiment
59% With boron trifluoride diethyl etherate In isopropyl alcohol at 120℃; for 17h; 129.1 820 mg (2.78 mmol) of t-butyl 3-oxo-4-(trifluoroacetyl)piperidin- 1 -carboxylate obtained in PREPARATION 47 and 585 mg (3.61mmol) of2,2,3, 3,3-pentafluoropropaneimidadide were added to 50 mL of isopropanol, then 101 of BF OEt (3%: catalyst amount) was dropwise added, and the resulting mixture was heated to 120°C and stirred for 17 hours. 1-2 drops of a saturated sodium bicarbonate was added at room temperature, followed by cooling to room temperature. Isopropanol was distilled off under reduced pressure and then the residue was purified by column chromatography (10:1 hexane:ethyl acetate) to give 690 mg of the title compound in a yield of 59%.[1802] 1H NMR (CDCl3) δ 4.84 (2H, s), 3.77 (2H, t, J=5.5 Hz), 3.11 (2H, br s), 1.50 (9H, s)[1803] Mass (m/e) 422 (M+l)
  • 2
  • [ 647863-25-0 ]
  • [ 733757-89-6 ]
YieldReaction ConditionsOperation in experiment
28% With hydrazine hydrate In ethanol at 50℃; for 24h; 7 A solution of 1-tert-butoxycarbonyl-4-(trifluoroacetyl)-3-piperidinone (D6, 23.6 g, 0.08 mol) in ethanol (250 ml) was treated with hydrazine monohydrate (4.16 ml, 0.086 mol). The mixture was allowed to stir at 50° C. for 24 h. The reaction mixture was cooled to room temperature and then evaporated under reduced pressure. The resulting mixture was partitioned between ethyl acetate and brine. The organic layer was separated and dried over sodium sulphate and evaporated under reduced pressure. Residual material was recrystallised from ethyl acetate/n-pentane to give the title compound as a pale yellow solid (6.5 g, 28%).1H-NMR (400 MHz, CDCl3) δ: 11.13 (1H, br s), 4.40 (2H, m), 3.66 (2H, m), 2.70 (2H, m), 1.48 (9H, s); LC/MS Retention time 2.90 mins/(ES-) 290 (M-H, C12H16F3N3O2 requires 291).
28% With hydrazine hydrate In ethanol at 50℃; for 24h;
28% With hydrazine In ethanol at 50℃; for 24h; 20 Description 20: 6-tert-butoxycarbonyl-3-(trifluoromethyl)-4,5,6,7-tetrahydro-1 H- pyrazolo[3,4-c]pyridineA solution of 1-tert-butoxycarbonyl-4-(trifluoroacetyl)-3-piperidinone (23.6g, O.Oδmol) in ethanol (250ml) was treated with hydrazine monohydrate (4.16ml, 0.086mol). The mixture was allowed to stir at 5O0C for 24h. The reaction mixture was cooled to room temperature and then evaporated under reduced pressure. The resulting mixture was partitioned between ethyl acetate and brine. The organic layer was separated and dried over sodium sulphate and evaporated under reduced pressure. Residual material was recrystallised from ethyl acetate / n-pentane to give the title compound as a pale yellow solid (6.5g, 28%).LC/MS (ES): Found 290 (ES-), retention time 2.90 mins. Ci2H16F3N3O2 requires 291.1 H-NMR (400MHz, CDCI3): 1.48 (9H, s), 2.70 (2H, m), 3.66 (2H, m), 4.40 (2H, m), 11.13 (1 H, br s),
With hydrazine In ethanol at 50℃; for 24h; 22 Description 22: 6-tert-butoxycarbonyl-3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H- pyrazolo[3,4-c]pyridine (D22); A solution of 1-tert-butoxycarbonyl-4-(trifluoroacetyl)-3-piperidinone (23.6g) in ethanol (250ml) was treated with hydrazine monohydrate (4.16ml, 0.086mol). The mixture was allowed to stir at 5O0C for 24h. The reaction mixture was cooled to room temperature and then evaporated under reduced pressure. The resulting mixture was partitioned between ethyl acetate and brine. The organic layer was separated and dried over sodium sulphate and evaporated under reduced pressure. Residual material was recrystallised from ethyl acetate / n-pentane to give the title compound as a pale yellow solid (6.5g, 28% over 2 steps).1 H-NMR (400MHz, CDCI3) δ: 11.13 (1 H, br s), 4.40 (2H, m), 3.66 (2H, m), 2.70 (2H, m), 1.48 (9H, s); LC/MS Retention time 2.90mins/(ES-) 290 (M-H, Ci2H16F3N3O2 requires 291 ).

  • 3
  • [ 647863-25-0 ]
  • [ 57297-29-7 ]
  • [ 911635-51-3 ]
YieldReaction ConditionsOperation in experiment
37% 1.27 g of sodiumethoxide (21 percentwt. Ethanol solution) was added at room temperature to a solution in which 500 mg (4.13 mmol) of cyclopropanecarbox- EPO <DP n="71"/>imidamide hydrochloric acid salt was dissolved in 50 mL of isopropanol. After stirring for 30 minutes, concentration and filtration was conducted, and 940 mg (3.17 mmol) of t-butyl 3-oxo-4-(trifluoroacetyl)piperidin-l-carboxylate obtained in PREPARATION 47 was added thereto, followed by addition of BF OEt 12 1 (3percent catalyst amount). The resulting solution was heated to 80°C, followed by stirring for 19 hours. After cooling to room temperature, isopropaneol was removed under reduced pressure. The residue was purified by column chromatography (10:1 hexane:ethyl acetate) to give 400 mg of the title compound in a yield of 37percent.[952] 1H NMR (CDCl3) delta 4.62 (2H, s), 3.68 (2H, t, J=5.5 Hz), 2.93 (2H, br s), 2.25 (IH, m), 1.49 (9H, s), 1.1-1.2 (4H, m)[953] Mass (m/e) 344 (M+l)
  • 4
  • [ 647863-25-0 ]
  • [ 71690-89-6 ]
  • [ 911637-92-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: cyclobutanecarboximidamide hydrochloride With sodium ethanolate In ethanol; isopropyl alcohol at 20℃; Stage #2: tert-butyl 3-oxo-4-(2,2,2-trifluoroacetyl) piperidine-1-carboxylate With boron trifluoride diethyl etherate In ethanol; isopropyl alcohol at 80℃; 4.2.1. Synthesis of intermediates 3 General procedure: 1.27 g of EtONa (21 %wt. Ethanol solution) was added at roomtemperature to a solution in which amidines hydrochloride 2 (4.13mmol) was dissolved in 50 mL of isopropanol. After stirring for 30 min,concentration and filtration was conducted, and commercially availablematerials tert-butyl 3-oxo-4-(2,2,2-trifluoroacetyl) piperidine-1-carboxylate 1 (940 mg, 3.17 mmol) was added, followed by additionof BF3OEt2 (3 % catalyst amount). The resulting solution was heated to80 C, followed by stirring for 18 h. After cooling to room temperature,isopropaneol was removed under reduced pressure. The residue waspurified by column chromatography (10: 1 hexane: Ethyl acetate) togive the intermediates 3 in a yield of 35-56 %
Stage #1: cyclobutanecarboximidamide hydrochloride With sodium ethanolate In ethanol; isopropyl alcohol at 20℃; Stage #2: tert-butyl 3-oxo-4-(2,2,2-trifluoroacetyl) piperidine-1-carboxylate With boron trifluoride diethyl etherate In ethanol; isopropyl alcohol at 80℃; 4.2.1. Synthesis of intermediates 3 General procedure: 1.27 g of EtONa (21 %wt. Ethanol solution) was added at roomtemperature to a solution in which amidines hydrochloride 2 (4.13mmol) was dissolved in 50 mL of isopropanol. After stirring for 30 min,concentration and filtration was conducted, and commercially availablematerials tert-butyl 3-oxo-4-(2,2,2-trifluoroacetyl) piperidine-1-carboxylate 1 (940 mg, 3.17 mmol) was added, followed by additionof BF3OEt2 (3 % catalyst amount). The resulting solution was heated to80 C, followed by stirring for 18 h. After cooling to room temperature,isopropaneol was removed under reduced pressure. The residue waspurified by column chromatography (10: 1 hexane: Ethyl acetate) togive the intermediates 3 in a yield of 35-56 %
  • 5
  • [ 647863-25-0 ]
  • [ 42518-06-9 ]
  • [ 911636-17-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-amidinopyridine hydrochloride With sodium ethanolate In ethanol; isopropyl alcohol at 20℃; Stage #2: tert-butyl 3-oxo-4-(2,2,2-trifluoroacetyl) piperidine-1-carboxylate With boron trifluoride diethyl etherate In ethanol; isopropyl alcohol at 80℃; 4.2.1. Synthesis of intermediates 3 General procedure: 1.27 g of EtONa (21 %wt. Ethanol solution) was added at roomtemperature to a solution in which amidines hydrochloride 2 (4.13mmol) was dissolved in 50 mL of isopropanol. After stirring for 30 min,concentration and filtration was conducted, and commercially availablematerials tert-butyl 3-oxo-4-(2,2,2-trifluoroacetyl) piperidine-1-carboxylate 1 (940 mg, 3.17 mmol) was added, followed by additionof BF3OEt2 (3 % catalyst amount). The resulting solution was heated to80 C, followed by stirring for 18 h. After cooling to room temperature,isopropaneol was removed under reduced pressure. The residue waspurified by column chromatography (10: 1 hexane: Ethyl acetate) togive the intermediates 3 in a yield of 35-56 %
Stage #1: 4-amidinopyridine hydrochloride With sodium ethanolate In ethanol; isopropyl alcohol at 20℃; Stage #2: tert-butyl 3-oxo-4-(2,2,2-trifluoroacetyl) piperidine-1-carboxylate With boron trifluoride diethyl etherate In ethanol; isopropyl alcohol at 80℃; 4.2.1. Synthesis of intermediates 3 General procedure: 1.27 g of EtONa (21 %wt. Ethanol solution) was added at roomtemperature to a solution in which amidines hydrochloride 2 (4.13mmol) was dissolved in 50 mL of isopropanol. After stirring for 30 min,concentration and filtration was conducted, and commercially availablematerials tert-butyl 3-oxo-4-(2,2,2-trifluoroacetyl) piperidine-1-carboxylate 1 (940 mg, 3.17 mmol) was added, followed by additionof BF3OEt2 (3 % catalyst amount). The resulting solution was heated to80 C, followed by stirring for 18 h. After cooling to room temperature,isopropaneol was removed under reduced pressure. The residue waspurified by column chromatography (10: 1 hexane: Ethyl acetate) togive the intermediates 3 in a yield of 35-56 %
 

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