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CAS No.: | 877399-74-1 |
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Name: | tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate |
Article Data: | 54 |
Molecular Structure: | |
Formula: | C19H32BN3O4 |
Molecular Weight: | 377.292 |
Synonyms: | 1-[1-(tert-Butoxycarbonyl)piperidin-4-yl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;4-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazol-1-yl)piperidine-1-carboxylicacid tert-butyl ester;4-[4-(4,4,5,5-Tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylicacid tert-butyl ester;tert-Butyl4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate;tert-Butyl4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazol-1-yl]piperidine-1-carboxylate; |
EINECS: | 800-459-4 |
Density: | 1.14 g/cm3 |
Melting Point: | 114.0 to 118.0 °C |
Boiling Point: | 492.803 °C at 760 mmHg |
Flash Point: | 251.838 °C |
PSA: | 65.82000 |
LogP: | 2.69220 |
4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester
bis(pinacol)diborane
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
Conditions | Yield |
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With C54H44NO2PPdS; potassium acetate In tetrahydrofuran at 80℃; for 24h; Miyaura Borylation Reaction; Inert atmosphere; Sealed tube; | 94% |
With isopropylmagnesium chloride In tetrahydrofuran at -10 - 30℃; for 9h; Inert atmosphere; Large scale; | 81% |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 80℃; for 0.166667h; Inert atmosphere; | 44% |
tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate
bis(pinacol)diborane
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
Conditions | Yield |
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With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In dimethyl sulfoxide at 80℃; for 2h; Inert atmosphere; | 87.9% |
With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In dimethyl sulfoxide at 80℃; for 2h; Inert atmosphere; | 87.9% |
With potassium acetate; tetrakis(triphenylphosphine) palladium(0) In dimethyl sulfoxide at 80℃; for 2h; Inert atmosphere; | 83% |
tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate
2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Stage #1: tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate With isopropylmagnesium chloride In tetrahydrofuran at -10 - 0℃; for 5.25h; Large scale reaction; Stage #2: 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 20 - 25℃; for 10.75h; Large scale reaction; | 81% |
Stage #1: tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate With isopropylmagnesium chloride In tetrahydrofuran at -10 - 20℃; for 2h; Inert atmosphere; Stage #2: 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; | 61.5% |
With isopropylmagnesium chloride In tetrahydrofuran at 0 - 30℃; | |
In tetrahydrofuran |
4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester
2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Stage #1: 4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at 20 - 30℃; for 12h; Stage #2: 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 20 - 30℃; for 6h; | 80% |
4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester
dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
Conditions | Yield |
---|---|
With potassium methanolate In 1,2-dimethoxyethane at 30℃; for 1h; | 61% |
4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Stage #1: 4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at 20 - 30℃; for 12h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 20 - 30℃; for 6h; | 60% |
With n-butyllithium In tetrahydrofuran; hexane at -70 - 20℃; for 3h; | 51% |
pyrazole-4-boronic acid pinacol ester
1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 20 - 100℃; for 18h; | 48% |
With caesium carbonate In N,N-dimethyl-formamide at 90℃; Inert atmosphere; | 44% |
With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; | 39% |
1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
Conditions | Yield |
---|---|
Stage #1: pyrazole-4-boronic acid pinacol ester With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: 1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate In N,N-dimethyl-formamide at 100℃; | 29% |
Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 110 °C / Inert atmosphere; Microwave irradiation 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / dimethyl sulfoxide / 3 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 4 °C / Inert atmosphere 1.2: 12 h / 100 °C / Inert atmosphere 2.1: bis-triphenylphosphine-palladium(II) chloride; potassium acetate / dimethyl sulfoxide / 2 h / 80 °C / Inert atmosphere View Scheme |
pyrazole-4-boronic acid pinacol ester
tert-butyl 4-bromo-1-piperidinecarboxylate
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl acetamide at 85℃; for 12h; Inert atmosphere; | 5% |
t-butyl 4-hydroxy piperidine-1-carboxylate
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate
Conditions | Yield |
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Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 110 °C / Inert atmosphere; Microwave irradiation 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / dimethyl sulfoxide / 3 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1.1: dmap; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 4 °C / Inert atmosphere 2.2: 12 h / 100 °C / Inert atmosphere 3.1: bis-triphenylphosphine-palladium(II) chloride; potassium acetate / dimethyl sulfoxide / 2 h / 80 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1.1: triethylamine / tert-butyl methyl ether / 1 h / -5 - 22 °C / Inert atmosphere 2.1: caesium carbonate / n-methyl-2-pyrrilidone / 18.5 h / 80 °C 3.1: isopropylmagnesium chloride / tetrahydrofuran / 5.25 h / -10 - 0 °C / Large scale reaction 3.2: 10.75 h / 20 - 25 °C / Large scale reaction View Scheme |
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The tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate is an organic compound with the formula C19H32BN3O4. The systematic name of this chemical is tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazol-1-yl]piperidine-1-carboxylate. With the CAS registry number 877399-74-1, it is also named as 1-piperidinecarboxylic acid, 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]-, 1,1-dimethylethyl ester.
Physical properties about tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate are: (1)#H bond acceptors: 7; (2)#Freely Rotating Bonds: 4; (3)Polar Surface Area: 65.82 Å2; (4)Index of Refraction: 1.539; (5)Molar Refractivity: 103.586 cm3; (6)Molar Volume: 330.852 cm3; (7)Polarizability: 41.065×10-24cm3; (8)Surface Tension: 37.581 dyne/cm; (9)Density: 1.14 g/cm3; (10)Flash Point: 251.838 °C; (11)Enthalpy of Vaporization: 75.981 kJ/mol; (12)Boiling Point: 492.803 °C at 760 mmHg.
You can still convert the following datas into molecular structure:
(1)SMILES: B1(OC(C(O1)(C)C)(C)C)c2cnn(c2)C3CCN(CC3)C(=O)OC(C)(C)C
(2)InChI: InChI=1/C19H32BN3O4/c1-17(2,3)25-16(24)22-10-8-15(9-11-22)23-13-14(12-21-23)20-26-18(4,5)19(6,7)27-20/h12-13,15H,8-11H2,1-7H3
(3)InChIKey: QSQWENQPOSRWLP-UHFFFAOYAI
(4)Std. InChI: InChI=1S/C19H32BN3O4/c1-17(2,3)25-16(24)22-10-8-15(9-11-22)23-13-14(12-21-23)20-26-18(4,5)19(6,7)27-20/h12-13,15H,8-11H2,1-7H3
(5)Std. InChIKey: QSQWENQPOSRWLP-UHFFFAOYSA-N