151213-42-2

Basic information

• Product Name: (S,S)-2,8-Diazabicyclo[4,3,0]nonane
• Synonyms: [S,S]-2,8-Diazabicyclo[4.3.0]Nonane98%;(S,S)-2,8-Diazabicyclo[4,3,0]onoane;(S,S)-2,8-DIAZABICYCLO[4,3,0]NONANE [FOR MOXIFLOXACIN];(1S,6S)-2,8-Diazacyclo[4,3,0]nonane ,99%;Moxifloxacin Intermediate 1;2,8-Diazabicyclo[4.3.0]nonane,Cis-Octahydropyrrolo[3,4-B]Pyridine;cis-Octahydropyrrolo[3,4-b]pyridine/(R,R)-2,8-Diazabicyclo[4,3,0]nonane;(1R,6R)-2,8-Diazabicyclo[4,3,0]nonane
• CAS NO: 151213-42-2
• Molecular Formula: C₇H₁₄N₂
• Molecular Weight: 126.2
• EINECS: 1806241-263-5
• Product Categories: pharmacetical;API intermediates;pharmaceutical intermediates;Heterocycle-Pyridine series
• Mol File: 151213-42-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 198.5 °C at 760 mmHg
• Flash Point: 87.1 °C
• Appearance: /
• Density: 0.95 g/cm³
• Vapor Pressure: 0.00209mmHg at 25°C
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly), Water
• PKA: 11.11±0.20(Predicted)
• CAS DataBase Reference: (S,S)-2,8-Diazabicyclo[4,3,0]nonane(CAS DataBase Reference)
• NIST Chemistry Reference: (S,S)-2,8-Diazabicyclo[4,3,0]nonane(151213-42-2)
• EPA Substance Registry System: (S,S)-2,8-Diazabicyclo[4,3,0]nonane(151213-42-2)

Safety Data

• Hazardous Substances Data: 151213-42-2(Hazardous Substances Data)

Usage

Chemical Properties

Clear light red liquid

Uses

(1R,6R)-2,8-Diazabicyclo[4.3.0]nonane is a chiral reagent used in the synthesis of pyrrolopyrimidine derivatives as dual DNA gyrase B and topoisomerase IV inhibitors and potential antibacterial agents.

InChI:InChI=1/C7H14N2.2ClH/c1-2-6-4-8-5-7(6)9-3-1;;/h6-9H,1-5H2;2*1H/t6-,7+;;/m0../s1

Synthetic route

[R,R]-8-benzyl-2,8-diazabicyclo[4.3.0]nonane (151213-43-3) → [R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2)

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

(R,R)-6-(toluene-4-sulfonyl)-octahydro-pyrrolo[3,4-b]pyridine (1038923-76-0) → [R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2)

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 → [R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2)

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 → [R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) + (1S,6S)-2,8-diazabicyclo[4.3.0]nonane (151213-40-0)

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

(S)-2-(6-methoxynaphthalen-2-yl)-1-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)propan-1-one (1558014-39-3) → [R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) + (1S,6S)-2,8-diazabicyclo[4.3.0]nonane (151213-40-0)

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

6-(2,4-dimethoxybenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine (1257241-37-4) → [R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) + (1S,6S)-2,8-diazabicyclo[4.3.0]nonane (151213-40-0)

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 → [R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2)

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

2,8-diazabicyclo-[4.3.0]-nonane (5654-94-4) → [R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2)

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

C18H25N3O → [R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2)

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

[R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) + 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid (112811-72-0) → moxifloxacin

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

[R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) + N-[2-amino-6-chloro-4-pyrimidinyl]-N-[3-fluoro-4-(1H-indazol-5-yloxy)phenyl]amine (688779-61-5) → 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	Yield
With N-ethyl-N,N-diisopropylamine In 2-Ethylhexyl alcohol at 150℃;	93%

[R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) + levofloxacin Q-acid (100986-89-8) → (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	Yield
With nano iron oxide on ZrO2 coated sulfonic acid In water for 0.45h; Reflux;	93%
at 150℃; Microwave irradiation;	89%

[R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) + 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid (86393-33-1) → 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	Yield
With nano iron oxide on ZrO2 coated sulfonic acid In water for 0.3h; Reflux;	91%
at 150℃; Microwave irradiation;	84%

[R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) + 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinoline carboxylic acid-O3,O4(bis(acyloxy-O)) borate (139693-52-0) → moxifloxacin hydrochloride (1394029-14-1)

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%

[R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) + 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	Yield
With N-ethyl-N,N-diisopropylamine In 2-Ethylhexyl alcohol at 150℃; for 3h;	14%

[R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) + 2-Amino-4,6-dichloropyrimidine (56-05-3) → C11H16ClN5

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

[R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) + 1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinoline carboxylic acid (O3,O4)bis(acyloxy-O)borate (139678-43-6) → (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	Yield
With triethylamine In acetonitrile for 1h; Heating / reflux;

[R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) → (R,R)-2,8-diazabicyclo[4.3.0]nonane dihydrobromide

Conditions	Yield
With hydrogen bromide In ethanol

[R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) + 2,4,8-trichloro-benzo[4,5]furo[3,2-d]pyrimidine (160199-00-8) → C17H16Cl2N4O (1345538-56-8)

Conditions	Yield
In ethanol

[R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) + trityl chloride (76-83-5) → C26H28N2

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;

[R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) → Reaxys ID: 29971796

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

[R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) → C25H30ClN3O3

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

[R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) → C35H37N3O

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

[R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) → C16H23N3O

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

[R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) → C23H27N3O2

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

[R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) → C35H36ClN3O

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

[R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) → C16H22ClN3O

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

[R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) → C24H28ClN3O3

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

[R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) → C12H15FN2OS

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

[R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) → C20H27FN2O2S

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

[R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) → C31H29FN2OS

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

[R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) → C13H18N2OS

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

[R,R]-2,8-diazabicyclo[4.3.0]nonane (151213-42-2) → C21H30N2O2S

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

Upstream product

• 5654-94-4 2,8-diazabicyclo-[4.3.0]-nonane 
• 1257241-37-4 6-(2,4-dimethoxybenzyl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine 
• 1558014-39-3 (S)-2-(6-methoxynaphthalen-2-yl)-1-(5H-pyrrolo[3,4-b]pyridin-6(7H)-yl)propan-1-one 
• 147740-02-1 6,7-dihydro-5H-pyrrolo[3,4-b]pyridine hydrochloride salt 
• 128740-14-7 8-benzyl-2,8-diazabicyclo[4.3.0]nonane 
• 1038923-76-0 (R,R)-6-(toluene-4-sulfonyl)-octahydro-pyrrolo[3,4-b]pyridine 
• 151213-43-3 [R,R]-8-benzyl-2,8-diazabicyclo[4.3.0]nonane 

Relevant articles and documents

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