(S,S)-2,8-Diazabicyclo[4,3,0]nonane supplier

Name
(S,S)-2,8-Diazabicyclo[4,3,0]nonane
EINECS 604-779-3
CAS No. 151213-42-2
Article Data7
CAS DataBase
Density 0.95 g/cm³
Solubility
Melting Point
Formula C₇H₁₄N₂
Boiling Point 198.5 °C at 760 mmHg
Molecular Weight 126.202
Flash Point 87.1 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1H-Pyrrolo[3,4-b]pyridine,octahydro-, (4aR-cis)-;(1R,6R)-2,8-Diazabicyclo[4.3.0]nonane;[(4AR,7aR)-Octahydro-6H-pyrrolo[3,4-b]pyridine;
PSA 24.06000
LogP 0.61540

Synthetic route

: 151213-43-3
[R,R]-8-benzyl-2,8-diazabicyclo[4.3.0]nonane

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

Conditions

Conditions	Yield
With hydrogen; 5%-palladium/activated carbon In methanol at 90℃; under 67506.8 Torr; for 5h;	85%
	9.61 g (85%)
	9.61 g (85%)
With palladium on activated charcoal; hydrogen In methanol

: 1038923-76-0
(R,R)-6-(toluene-4-sulfonyl)-octahydro-pyrrolo[3,4-b]pyridine

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

Conditions

Conditions	Yield
Stage #1: (R,R)-6-(toluene-4-sulfonyl)-octahydro-pyrrolo[3,4-b]pyridine With hydrogen bromide; propionic acid; phenol In water for 6 - 7h; Heating / reflux; Stage #2: With sodium hydroxide In water pH=11 - 12;	80.1%

: 8-benzyl-2,8-diazabicyclo[4.3.0]nonane

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: D-tartaric acid / N,N-dimethyl-formamide; 2-methoxy-ethanol 2: palladium on activated charcoal; hydrogen / methanol View Scheme

: 6,7-dihydro-5H-pyrrolo[3,4-b]pyridine hydrochloride salt

A: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

B: 151213-40-0
(1S,6S)-2,8-diazabicyclo[4.3.0]nonane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 25 - 35 °C 2.1: hydrogen; 5%-palladium/activated carbon / toluene / 24 h / 80 °C / 6000.6 Torr 2.2: Reflux View Scheme

: 1558014-39-3
(S)-2-(6-methoxynaphthalen-2-yl)-1-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)propan-1-one

A: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

B: 151213-40-0
(1S,6S)-2,8-diazabicyclo[4.3.0]nonane

Conditions

Conditions	Yield
Stage #1: (S)-2-(6-methoxynaphthalen-2-yl)-1-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)propan-1-one With 5%-palladium/activated carbon; hydrogen In toluene at 80℃; under 6000.6 Torr; for 24h; Stage #2: With hydrogen bromide; phenol In acetic acid; propionic acid Reflux;	A n/a B n/a

: 1257241-37-4
6-(2,4-dimethoxybenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine

A: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

B: 151213-40-0
(1S,6S)-2,8-diazabicyclo[4.3.0]nonane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: trifluoroacetic acid; triethylsilane / 4 h / 60 - 65 °C 1.2: 20 °C 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 25 - 35 °C 3.1: hydrogen; 5%-palladium/activated carbon / toluene / 24 h / 80 °C / 6000.6 Torr 3.2: Reflux View Scheme

: C14H16N2O

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; boron trifluoride-tetrahydrofuran complex / tetrahydrofuran / -5 - 20 °C 2: palladium 10% on activated carbon; hydrogen / ethanol / 40 °C / 2250.23 - 3750.38 Torr 3: L-Tartaric acid / isopropyl alcohol; water / 20 - 80 °C View Scheme

: 5654-94-4
2,8-diazabicyclo-[4.3.0]-nonane

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

Conditions

Conditions	Yield
With L-Tartaric acid In water; isopropyl alcohol at 20 - 80℃;	3.8 g

: C18H25N3O

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: ethyl acetate / 70 °C 2: sodium tetrahydroborate; boron trifluoride-tetrahydrofuran complex / tetrahydrofuran / -5 - 20 °C 3: palladium 10% on activated carbon; hydrogen / ethanol / 40 °C / 2250.23 - 3750.38 Torr 4: L-Tartaric acid / isopropyl alcohol; water / 20 - 80 °C View Scheme

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

: 112811-72-0
1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid

: moxifloxacin

Conditions

Conditions	Yield
With nano iron oxide on ZrO2 coated sulfonic acid In water for 0.416667h; Reflux;	96%
at 150℃; Microwave irradiation;	83%

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

: 688779-61-5
N-[2-amino-6-chloro-4-pyrimidinyl]-N-[3-fluoro-4-(1H-indazol-5-yloxy)phenyl]amine

: 6-[(4aR,7aR)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-N4-[3-fluoro-4-(1H-indazol-5-yloxy)phenyl]-2,4-pyrimidinediamine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 2-Ethylhexyl alcohol at 150℃;	93%

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

: 100986-89-8
levofloxacin Q-acid

: (3S)-9-fluoro-10-{(4aR,7aR)-hexahydro-1H-pyrrolo[3,4-b]-pyridin-6(2H)-yl}-3-methyl-7-oxo-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid

Conditions

Conditions	Yield
With nano iron oxide on ZrO2 coated sulfonic acid In water for 0.45h; Reflux;	93%
at 150℃; Microwave irradiation;	89%

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

: 86393-33-1
7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid

: 1-cyclopropyl-6-fluoro-7-{(4aR,7aR)-hexahydro-1H-pyrrolo[3,4-b]pyridin-6(2H)-yl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Conditions

Conditions	Yield
With nano iron oxide on ZrO2 coated sulfonic acid In water for 0.3h; Reflux;	91%
at 150℃; Microwave irradiation;	84%

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

: 139693-52-0
1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinoline carboxylic acid-O3,O4(bis(acyloxy-O)) borate

: 1394029-14-1
moxifloxacin hydrochloride

Conditions

Conditions	Yield
Stage #1: [R,R]-2,8-diazabicyclo[4.3.0]nonane; 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinoline carboxylic acid-O3,O4(bis(acyloxy-O)) borate With triethylamine In acetonitrile at 15 - 30℃; for 8h; Stage #2: With hydrogenchloride In methanol at 15 - 20℃; Temperature;	71%

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

: N-{4-[(3-amino-1,2-benzisoxazol-4-yl)oxy]-3-fluorophenyl}-N-(2-amino-6-chloro-4-pyrimidinyl)amine

: 4-[(4aR,7aR)-octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-6-({4-[(3-amino-1,2-benzisoxazol-4-yl)oxy]-3-fluorophenyl}amino)-2-pyrimidinylamine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In 2-Ethylhexyl alcohol at 150℃; for 3h;	14%

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

: 56-05-3
2-Amino-4,6-dichloropyrimidine

: C11H16ClN5

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 60℃; for 2h;

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

: 139678-43-6
1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinoline carboxylic acid (O3,O4)bis(acyloxy-O)borate

: (4aS-cis)-1-cyclopropyl-7-(2,8-diazabicyclo[4.3.0]non-8-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid (O3,O3)bis(acyloxy-O)borate

Conditions

Conditions	Yield
With triethylamine In acetonitrile for 1h; Heating / reflux;

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

: (R,R)-2,8-diazabicyclo[4.3.0]nonane dihydrobromide

Conditions

Conditions	Yield
With hydrogen bromide In ethanol

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

: 160199-00-8
2,4,8-trichloro-benzo[4,5]furo[3,2-d]pyrimidine

: 1345538-56-8
C17H16Cl2N4O

Conditions

Conditions	Yield
In ethanol

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

: 76-83-5
trityl chloride

: C26H28N2

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 3h; Cooling with ice;
With triethylamine In N,N-dimethyl-formamide at 20℃; for 3h; Cooling with ice;
With triethylamine In N,N-dimethyl-formamide at 20℃; for 3h; Cooling with ice;

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

Reaxys ID: 29971796: Reaxys ID: 29971796

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Cooling with ice 2: N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux 3: hydrogenchloride / methanol; water / 5 h / 20 °C 4: dicyclohexyl-carbodiimide View Scheme

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

: C25H30ClN3O3

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Cooling with ice 2: N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux 3: hydrogenchloride / methanol; water / 5 h / 20 °C 4: dicyclohexyl-carbodiimide; dmap / tetrahydrofuran / 20 °C View Scheme

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

: C35H37N3O

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Cooling with ice 2: N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Cooling with ice 2: N,N-dimethyl-formamide / 1 h / Reflux; Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Cooling with ice 2: N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C 2: N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C 2: N,N-dimethyl-formamide / 1 h / Reflux; Inert atmosphere View Scheme

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

: C16H23N3O

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Cooling with ice 2: N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux 3: hydrogenchloride / methanol; water / 5 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Cooling with ice 2: N,N-dimethyl-formamide / 1 h / Reflux; Inert atmosphere 3: hydrogenchloride / methanol / 5 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Cooling with ice 2: N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux 3: hydrogenchloride / water; methanol / 5 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C 2: N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux 3: hydrogenchloride / methanol; water / 5 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C 2: N,N-dimethyl-formamide / 1 h / Reflux; Inert atmosphere 3: hydrogenchloride / methanol; water / 5 h / 20 °C View Scheme

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

: C23H27N3O2

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Cooling with ice 2: N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux 3: hydrogenchloride / methanol; water / 5 h / 20 °C 4: dicyclohexyl-carbodiimide; dmap / tetrahydrofuran / 20 °C View Scheme
Multi-step reaction with 4 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Cooling with ice 2: N,N-dimethyl-formamide / 1 h / Reflux; Inert atmosphere 3: hydrogenchloride / methanol / 5 h / 20 °C 4: dmap; dicyclohexyl-carbodiimide / tetrahydrofuran / 20 °C View Scheme
Multi-step reaction with 4 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Cooling with ice 2: N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux 3: hydrogenchloride / methanol; water / 5 h / 20 °C 4: dmap; dicyclohexyl-carbodiimide / tetrahydrofuran / 20 °C View Scheme

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

: C35H36ClN3O

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Cooling with ice 2: N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C 2: N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C 2: N,N-dimethyl-formamide / 1 h / Reflux; Inert atmosphere View Scheme

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

: C16H22ClN3O

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Cooling with ice 2: N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux 3: hydrogenchloride / methanol; water / 5 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C 2: N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux 3: hydrogenchloride / methanol; water / 5 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C 2: N,N-dimethyl-formamide / 1 h / Reflux; Inert atmosphere 3: hydrogenchloride / methanol; water / 5 h / 20 °C View Scheme

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

: C24H28ClN3O3

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Cooling with ice 2: N,N-dimethyl-formamide / 1 h / Inert atmosphere; Reflux 3: hydrogenchloride / methanol; water / 5 h / 20 °C 4: dicyclohexyl-carbodiimide; dmap / tetrahydrofuran / 20 °C View Scheme

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

: C12H15FN2OS

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Cooling with ice 2: dmap; dicyclohexyl-carbodiimide / tetrahydrofuran / 20 °C 3: hydrogenchloride / water; methanol / 5 h / 20 °C View Scheme

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

: C20H27FN2O2S

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Cooling with ice 2: dmap; dicyclohexyl-carbodiimide / tetrahydrofuran / 20 °C 3: hydrogenchloride / water; methanol / 5 h / 20 °C 4: dmap; dicyclohexyl-carbodiimide / tetrahydrofuran / 20 °C View Scheme

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

: C31H29FN2OS

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Cooling with ice 2: dmap; dicyclohexyl-carbodiimide / tetrahydrofuran / 20 °C View Scheme

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

: C13H18N2OS

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Cooling with ice 2: dmap; dicyclohexyl-carbodiimide / tetrahydrofuran / 20 °C 3: hydrogenchloride / water; methanol / 5 h / 20 °C View Scheme

: 151213-42-2
[R,R]-2,8-diazabicyclo[4.3.0]nonane

: C21H30N2O2S

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Cooling with ice 2: dmap; dicyclohexyl-carbodiimide / tetrahydrofuran / 20 °C 3: hydrogenchloride / water; methanol / 5 h / 20 °C 4: dmap; dicyclohexyl-carbodiimide / tetrahydrofuran / 20 °C View Scheme

(S,S)-2,8-Diazabicyclo[4,3,0]nonane Chemical Properties

Product Name: 1H-Pyrrolo[3,4-b]pyridine,octahydro-, (4aR,7aR)- (CAS NO.151213-42-2)

Molecular Formula: C₇H₁₄N₂
Molecular Weight: 126.2g/mol
Mol File: 151213-42-2.mol
Boiling point: 198.5 °C at 760 mmHg
Flash Point: 87.1 °C
Density: 0.95 g/cm³
Surface Tension: 31.5 dyne/cm
Enthalpy of Vaporization: 43.47 kJ/mol
Vapour Pressure: 0.358 mmHg at 25°C
Product Categories: pharmacetical; API intermediates; pharmaceutical intermediates

(S,S)-2,8-Diazabicyclo[4,3,0]nonane Specification

1H-Pyrrolo[3,4-b]pyridine,octahydro-, (4aR,7aR)- , its CAS NO. is 151213-42-2, the synonym is (4aR,7aR)-octahydro-1H-pyrrolo[3,4-b]pyridine .

Product Name

(S,S)-2,8-Diazabicyclo[4,3,0]nonane

Synthetic route

(S,S)-2,8-Diazabicyclo[4,3,0]nonane Chemical Properties

(S,S)-2,8-Diazabicyclo[4,3,0]nonane Specification

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