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274693-55-9

Basic Information
CAS No.: 274693-55-9
Name: 1-Acetyladamantane Intermediate
Article Data: 17
Molecular Structure:
Molecular Structure of 274693-55-9 (1-Acetyladamantane Intermediate)
Formula: C10H19NO4
Molecular Weight: 217.265
Synonyms: Ticagrelor Intermediate1;
EINECS: 1312995-182-4
Density: 1.21 g/cm3
Boiling Point: 338.144 °C at 760 mmHg
Flash Point: 158.304 °C
PSA: 73.94000
LogP: 0.31530
Synthetic route
274693-54-8

benzyl 6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-ylcarbamate

274693-55-9

[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol99%
With 5%-palladium/activated carbon In methanol at 20℃; for 1h;75.7%
palladium on charcoal In ethanol

C17H25NO4

274693-55-9

[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In ethanol at 50 - 60℃; under 750.075 Torr; for 12h; Autoclave; Inert atmosphere;98%
With palladium on activated charcoal; hydrogen; acetic acid In methanol at 20℃; under 3750.38 - 6000.6 Torr; for 10h;92.8%

C10H16O5

274693-55-9

[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions
ConditionsYield
With hydrogenchloride; pyridoxal 5'-phosphate; isopropylamine; triethylamine In water at 25℃; for 16h; pH=8; Solvent; Reagent/catalyst; Temperature; Large scale; Enzymatic reaction;97%

C15H27NO6

274693-55-9

[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions
ConditionsYield
In ethylene glycol at 120℃; for 8h; Solvent; Temperature;92%

C17H24N2O6

274693-55-9

[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen; acetic acid In methanol at 20℃; for 14h;91.5%
1444301-50-1

(3aS,4R,6S,6aR)-N-benzyl-6-(2-(benzyloxy)ethoxy)-2,2-dimethyl-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-amine

274693-55-9

[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 40℃; under 7500.75 Torr; for 168h;63%
345898-95-5

N-(((4S,5R)-2,2-dimethyl-5-vinyl-1 ,3-dioxolan-4-yl)methylene)-1-phenylmethanamine oxide

274693-55-9

[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: N,N-dimethyl-formamide; toluene / 5 h / 110 °C
2.1: palladium 10% on activated carbon; hydrogen / methanol / 14 h / 20 °C
3.1: N-ethyl-N,N-diisopropylamine / 4-methyl-2-pentanone / 2 h / 20 °C
4.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C
4.2: 3 h / 20 °C
5.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C
6.1: 5%-palladium/activated carbon / methanol / 1 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: toluene / 5 h / Reflux
2.1: zinc; acetic acid / diethyl ether / 72.48 h / 0 - 25 °C
3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere
3.2: 4 h / 0 - 20 °C / Inert atmosphere
4.1: palladium 10% on activated carbon; hydrogen / methanol / 168 h / 40 °C / 7500.75 Torr
View Scheme
Multi-step reaction with 6 steps
1.1: N,N-dimethyl-formamide / 2 h / Reflux
2.1: ammonium formate; palladium 10% on activated carbon / methanol / 1.5 h / Reflux
3.1: potassium carbonate / water / 5.5 h / 20 °C
4.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -20 °C
4.2: 6.33 h / -20 - 20 °C
5.1: sodium tetrahydroborate; ethanol / 4 h / 60 °C
6.1: ammonium formate; palladium 10% on activated carbon / ethanol / 1 h / 40 °C
View Scheme

ethyl 2-(6-(benzyloxycarbonylamino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy) acetate

274693-55-9

[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C
2: 5%-palladium/activated carbon / methanol / 1 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: lithium borohydride / tetrahydrofuran / 0 - 20 °C
1.2: 20 °C
1.3: pH 6 - 7
2.1: ammonium formate / palladium 10% on activated carbon / ethanol / 30 - 70 °C
View Scheme
274693-53-7

[3aS-(3aα,4α,6α,6aα)]-(tetrahydro-6-hydroxy-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl)carbamic acid phenylmethyl ester

274693-55-9

[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C
1.2: 3 h / 20 °C
2.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C
3.1: 5%-palladium/activated carbon / methanol / 1 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: potassium tert-butylate / tetrahydrofuran / 0 °C
2.1: lithium borohydride / tetrahydrofuran / 0 - 20 °C
2.2: 20 °C
2.3: pH 6 - 7
3.1: ammonium formate / palladium 10% on activated carbon / ethanol / 30 - 70 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium tert-butylate
2: hydrogen / palladium on activated charcoal / ethanol
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / -20 °C
1.2: 6.33 h / -20 - 20 °C
2.1: sodium tetrahydroborate; ethanol / 4 h / 60 °C
3.1: ammonium formate; palladium 10% on activated carbon / ethanol / 1 h / 40 °C
View Scheme
274693-55-9

[3aR-(3aα,4α,6α,6aα)]-2-[[6-amino-2,2-dimethyl tetrahydro-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: pyridine / 24 h / 20 °C
2.1: sodium iodide / butanone / 24 h / 120 °C
3.1: zinc / ethanol / 1 h / 70 °C
4.1: sodium carbonate / ethanol / 1 h / 50 °C
5.1: N,N-dimethyl-formamide; toluene / 5 h / 110 °C
6.1: palladium 10% on activated carbon; hydrogen / methanol / 14 h / 20 °C
7.1: N-ethyl-N,N-diisopropylamine / 4-methyl-2-pentanone / 2 h / 20 °C
8.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / -30 °C
8.2: 3 h / 20 °C
9.1: lithium borohydride / tetrahydrofuran / 5 h / 0 °C
10.1: 5%-palladium/activated carbon / methanol / 1 h / 20 °C
View Scheme
Multi-step reaction with 8 steps
1.1: pyridine / 4 h / -10 - -5 °C
2.1: lithium bromide / butanone / 22 h / 80 °C
3.1: hydrogenchloride; zinc/copper couple / water; methanol / 18 h / 25 °C
4.1: sodium carbonate / methanol / 0.5 h / 25 °C
5.1: toluene / 5 h / Reflux
6.1: zinc; acetic acid / diethyl ether / 72.48 h / 0 - 25 °C
7.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere
7.2: 4 h / 0 - 20 °C / Inert atmosphere
8.1: palladium 10% on activated carbon; hydrogen / methanol / 168 h / 40 °C / 7500.75 Torr
View Scheme
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274693-27-5
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  • 2-[[(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

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    274693-55-9

    2-[[(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]ethanol

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    1-Acetyladamantane Intermediate

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  • Casno:

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    TIANFUCHEM-- 1-Acetyladamantane Intermediate

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Specification

The Ticagrelor Intermediate1, with CAS registry number 274693-55-9, has the systematic name of 2-{[(3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]oxy}ethanol; 1-Acetyladamantane Intermediate;2-(6-Amino-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yloxy)-ethanol;. Besides this, it is also called 1-Acetyladamantane Intermediate. And the chemical formula of this chemical is C10H19NO4.

Physical properties of Ticagrelor Intermediate1: (1)ACD/LogP: -1.48; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 5; (4)#H bond donors: 3; (5)#Freely Rotating Bonds: 5; (6)Polar Surface Area: 73.94 Å2; (7)Index of Refraction: 1.52; (8)Molar Refractivity: 54.561 cm3; (9)Molar Volume: 179.494 cm3; (10)Polarizability: 21.63×10-24cm3; (11)Surface Tension: 45.976 dyne/cm; (12)Density: 1.21 g/cm3; (13)Flash Point: 158.304 °C; (14)Enthalpy of Vaporization: 67.36 kJ/mol; (15)Boiling Point: 338.144 °C at 760 mmHg; (16)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O1[C@H]2[C@H](N)C[C@H](OCCO)[C@H]2OC1(C)C
(2)InChI: InChI=1/C10H19NO4/c1-10(2)14-8-6(11)5-7(9(8)15-10)13-4-3-12/h6-9,12H,3-5,11H2,1-2H3/t6-,7+,8+,9-/m1/s1
(3)InChIKey: WNYYMPICYAOQAE-RYPBNFRJBV
(4)Std. InChI: InChI=1S/C10H19NO4/c1-10(2)14-8-6(11)5-7(9(8)15-10)13-4-3-12/h6-9,12H,3-5,11H2,1-2H3/t6-,7+,8+,9-/m1/s1
(5)Std. InChIKey: WNYYMPICYAOQAE-RYPBNFRJSA-N