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423165-08-6

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Basic Information
CAS No.: 423165-08-6
Name: 3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane-p-toluenesulfonate
Article Data: 4
Molecular Structure:
Molecular Structure of 423165-08-6 (3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane-p-toluenesulfonate)
Formula: C20H30N4O3S
Molecular Weight: 406.549
Synonyms: 3-[3-methyl-5-(propan-2-yl)-4H-1,2,4-triazol-4-yl]-8-azabicyclo[3.2.1]octane 4-methylbenzenesulfonate (1:1);
Boiling Point: 402.4 °C at 760 mmHg
Flash Point: 197.1 °C
PSA: 105.49000
LogP: 4.81670
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Synthetic route
423165-13-3

exo-8-benzyl-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane

104-15-4

toluene-4-sulfonic acid

423165-08-6

exo-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane p-toluenesulfonate

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen In methanol at 50℃; under 2250.23 Torr; Solvent; Time; Inert atmosphere; Large scale;92%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 2585.81 Torr; Inert atmosphere;86%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 6723.1 Torr; for 17h;80%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃;80%
76272-34-9

8-Benzyl-1αH,5αH-nortropan-3-one Oxime

423165-08-6

exo-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane p-toluenesulfonate

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: sodium; propan-1-ol / toluene / 12 h / Reflux; Inert atmosphere
2: tetrahydrofuran / 72 h / 20 °C / Inert atmosphere
3: hydrogenchloride / methanol; 1,4-dioxane / 2 h / 20 °C / Inert atmosphere
4: sodium carbonate / water; dichloromethane / 0 - 20 °C / Inert atmosphere
5: phosphorus pentachloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
6: dichloromethane; tert-Amyl alcohol / 0 - 20 °C / Inert atmosphere
7: acetic acid / ethyl acetate / 0.5 h / 80 °C / Inert atmosphere
8: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2585.81 Torr / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: sodium / pentan-1-ol / 4 h / Reflux
2.1: sodium carbonate / dichloromethane / 2.5 h / 0 - 20 °C
3.1: phosphorus pentachloride; pyridine / dichloromethane / 4 h / 20 °C / Inert atmosphere; Cooling with ice
3.2: 17.5 h / 0 - 20 °C / Inert atmosphere
3.3: 2 h / Inert atmosphere; Reflux
4.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C
View Scheme

8-benzyl-8-azabicyclo[3.2.1]octan-3-amine

423165-08-6

exo-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane p-toluenesulfonate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: tetrahydrofuran / 72 h / 20 °C / Inert atmosphere
2: hydrogenchloride / methanol; 1,4-dioxane / 2 h / 20 °C / Inert atmosphere
3: sodium carbonate / water; dichloromethane / 0 - 20 °C / Inert atmosphere
4: phosphorus pentachloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
5: dichloromethane; tert-Amyl alcohol / 0 - 20 °C / Inert atmosphere
6: acetic acid / ethyl acetate / 0.5 h / 80 °C / Inert atmosphere
7: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2585.81 Torr / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: sodium carbonate / dichloromethane / 2.5 h / 0 - 20 °C
2.1: phosphorus pentachloride; pyridine / dichloromethane / 4 h / 20 °C / Inert atmosphere; Cooling with ice
2.2: 17.5 h / 0 - 20 °C / Inert atmosphere
2.3: 2 h / Inert atmosphere; Reflux
3.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C
View Scheme
132259-54-2

exo-(8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl)-carbamic acid tert-butyl ester

423165-08-6

exo-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane p-toluenesulfonate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: hydrogenchloride / methanol; 1,4-dioxane / 2 h / 20 °C / Inert atmosphere
2: sodium carbonate / water; dichloromethane / 0 - 20 °C / Inert atmosphere
3: phosphorus pentachloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
4: dichloromethane; tert-Amyl alcohol / 0 - 20 °C / Inert atmosphere
5: acetic acid / ethyl acetate / 0.5 h / 80 °C / Inert atmosphere
6: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2585.81 Torr / Inert atmosphere
View Scheme

N-((1R,3S,5S)-8-Benzyl-8-aza-bicyclo[3.2.1]oct-3-yl)-2-methyl-propionimidoyl chloride

423165-08-6

exo-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane p-toluenesulfonate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dichloromethane; tert-Amyl alcohol / 0 - 20 °C / Inert atmosphere
2: acetic acid / ethyl acetate / 0.5 h / 80 °C / Inert atmosphere
3: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2585.81 Torr / Inert atmosphere
View Scheme
76272-36-1

8-benzyl-8-aza-bicyclo[3.2.1]oct-3-yl-amine

423165-08-6

exo-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane p-toluenesulfonate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium carbonate / water; dichloromethane / 0 - 20 °C / Inert atmosphere
2: phosphorus pentachloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
3: dichloromethane; tert-Amyl alcohol / 0 - 20 °C / Inert atmosphere
4: acetic acid / ethyl acetate / 0.5 h / 80 °C / Inert atmosphere
5: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2585.81 Torr / Inert atmosphere
View Scheme
376348-67-3

exo-N-(8-benzyl-8-azabicyclo[3.2.1]oct-3-yl)-2-methylpropanamide

423165-08-6

exo-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane p-toluenesulfonate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: phosphorus pentachloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
2: dichloromethane; tert-Amyl alcohol / 0 - 20 °C / Inert atmosphere
3: acetic acid / ethyl acetate / 0.5 h / 80 °C / Inert atmosphere
4: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2585.81 Torr / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: phosphorus pentachloride; pyridine / dichloromethane / 4 h / 20 °C / Inert atmosphere; Cooling with ice
1.2: 17.5 h / 0 - 20 °C / Inert atmosphere
1.3: 2 h / Inert atmosphere; Reflux
2.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C
View Scheme
28957-72-4

N-benzylnortropinone

423165-08-6

exo-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane p-toluenesulfonate

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: hydroxylamine hydrochloride; sodium hydroxide / ethanol; water / 20 h / Inert atmosphere; Reflux
2: sodium; propan-1-ol / toluene / 12 h / Reflux; Inert atmosphere
3: tetrahydrofuran / 72 h / 20 °C / Inert atmosphere
4: hydrogenchloride / methanol; 1,4-dioxane / 2 h / 20 °C / Inert atmosphere
5: sodium carbonate / water; dichloromethane / 0 - 20 °C / Inert atmosphere
6: phosphorus pentachloride / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
7: dichloromethane; tert-Amyl alcohol / 0 - 20 °C / Inert atmosphere
8: acetic acid / ethyl acetate / 0.5 h / 80 °C / Inert atmosphere
9: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 2585.81 Torr / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: hydroxylamine hydrochloride; sodium hydrogencarbonate / water; ethanol / 2 h / Inert atmosphere
2.1: sodium / pentan-1-ol / 4 h / Reflux
3.1: sodium carbonate / dichloromethane / 2.5 h / 0 - 20 °C
4.1: phosphorus pentachloride; pyridine / dichloromethane / 4 h / 20 °C / Inert atmosphere; Cooling with ice
4.2: 17.5 h / 0 - 20 °C / Inert atmosphere
4.3: 2 h / Inert atmosphere; Reflux
5.1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C
View Scheme

(-)-(3S)-3-benzyloxycarbonylamino-3-phenylpropanal

423165-08-6

exo-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane p-toluenesulfonate

376348-80-0

benzyl (S)-3-((1R,3R,5S)-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl)-1-phenylpropylcarbamate

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; Inert atmosphere;93%
376348-78-6

4,4-difluorocyclohexanecarboxylic acid (3-oxo-1-phenyl-propyl)-amide

423165-08-6

exo-3-(3-isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane p-toluenesulfonate

376348-65-1

maraviroc

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In ethyl acetate at 0 - 15℃; for 2h; Inert atmosphere; Large scale;91%
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; Inert atmosphere; optical yield given as %ee;78%
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  • 3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane-p-toluenesulfonate

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    423165-08-6

    3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane-p-toluenesulfonate

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  • 423165-08-6

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    423165-08-6

    423165-08-6

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  • 3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-aza

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    423165-08-6

    3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-aza

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  • 3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane 4-methylbenzenesulfonate

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    423165-08-6

    3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octane 4-methylbenzenesulfonate

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Specification

The 3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]]octane P-Toluenesulfonate has the CAS registry number 423165-08-6. This chemical's molecular formula is C20H30N4O3S and molecular weight is 406.54. What's more, its systematic name is 3-[3-methyl-5-(propan-2-yl)-4H-1,2,4-triazol-4-yl]-8-azabicyclo[3.2.1]octane 4-methylbenzenesulfonate (1:1).

Physical properties of 3-(3-Isopropyl-5-methyl-4H-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]]octane P-Toluenesulfonate are: (1)ACD/LogP: 1.14; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2; (4)ACD/LogD (pH 7.4): -2; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 33.95 Å2; (13)Flash Point: 197.1 °C; (14)Enthalpy of Vaporization: 65.35 kJ/mol; (15)Boiling Point: 402.4 °C at 760 mmHg; (16)Vapour Pressure: 1.1E-06 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: O=S(=O)(O)c1ccc(cc1)C.n1nc(n(c1C)C3CC2NC(CC2)C3)C(C)C
(2)InChI: InChI=1/C13H22N4.C7H8O3S/c1-8(2)13-16-15-9(3)17(13)12-6-10-4-5-11(7-12)14-10;1-6-2-4-7(5-3-6)11(8,9)10/h8,10-12,14H,4-7H2,1-3H3;2-5H,1H3,(H,8,9,10)
(3)InChIKey: BVRVOZLPVSXSLY-UHFFFAOYAH