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

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

Uses

Used in Pharmaceutical Industry:
(S,S)-2,8-Diazabicyclo[4,3,0]nonane is used as a chiral reagent for the synthesis of pyrrolopyrimidine derivatives. These derivatives serve as dual DNA gyrase B and topoisomerase IV inhibitors, making them potential antibacterial agents. The compound's chiral nature allows for the creation of specific drug candidates with targeted effects, contributing to the development of novel antibiotics to combat bacterial resistance.

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

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

Relevant articles and documents

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