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877399-74-1

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Basic Information
CAS No.: 877399-74-1
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:
Molecular Structure of 877399-74-1 (tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate)
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
Related products
Synthetic route
877399-50-3

4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester

73183-34-3

bis(pinacol)diborane

877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
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%
877399-73-0

tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate

73183-34-3

bis(pinacol)diborane

877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
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%
877399-73-0

tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate

1195-66-0

2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
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
877399-50-3

4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester

1195-66-0

2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
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%
877399-50-3

4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester

185990-03-8

dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane

877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With potassium methanolate In 1,2-dimethoxyethane at 30℃; for 1h;61%
877399-50-3

4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester

61676-62-8

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
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%
269410-08-4

pyrazole-4-boronic acid pinacol ester

141699-59-4

1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate

877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
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%
141699-59-4

1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate

877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
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
269410-08-4

pyrazole-4-boronic acid pinacol ester

180695-79-8

tert-butyl 4-bromo-1-piperidinecarboxylate

877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl acetamide at 85℃; for 12h; Inert atmosphere;5%
109384-19-2

t-butyl 4-hydroxy piperidine-1-carboxylate

877399-74-1

tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions
ConditionsYield
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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Specification

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