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Chemical Structure| 504-12-1 Chemical Structure| 504-12-1

Structure of 504-12-1

Chemical Structure| 504-12-1

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Product Details of [ 504-12-1 ]

CAS No. :504-12-1
Formula : C8H15NO
M.W : 141.21
SMILES Code : OC1CC(N2)CCCC2C1
MDL No. :MFCD07780804
InChI Key :LAZFLHAAIKYNNV-DHBOJHSNSA-N
Pubchem ID :12310339

Safety of [ 504-12-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Application In Synthesis of [ 504-12-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 504-12-1 ]

[ 504-12-1 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 108-24-7 ]
  • [ 504-12-1 ]
  • [ 36079-69-3 ]
  • 2
  • [ 98-88-4 ]
  • [ 504-12-1 ]
  • 9-benzoyl-9-aza-bicyclo[3.3.1]nonane-3<i>endo</i>-ol [ No CAS ]
  • 3
  • methylammonium carbonate [ No CAS ]
  • [ 504-12-1 ]
  • 3<i>endo</i>-hydroxy-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid [ No CAS ]
  • 4
  • (3-endo)-9-methyl-9-azabicyclo[3.3.1]nonan-3-ol [ No CAS ]
  • [ 504-12-1 ]
  • 7
  • [ 552-70-5 ]
  • [ 504-12-1 ]
  • 8
  • [ 24424-99-5 ]
  • [ 504-12-1 ]
  • [ 934180-37-7 ]
YieldReaction ConditionsOperation in experiment
83% With sodium hydroxide; In 1,4-dioxane; water; at -15 - 20℃; for 4.16667h; Crude enαto-9-azabicyclo[3.3.1]nonan-3-ol (from Step c) was dissolved in a solution of dioxane (500 ml_), water (187.5 ml.) and 4N sodium hydroxide (aq.) (62.5 ml.) and cooled to -15 0C under a nitrogen atmosphere. Di-terf-butyl dicarbonate (39.0 g, 0.18 mol) was added portionwise over 10 min, the reaction mixture allowed to warm to ambient temperature and stirring continued for 4 h during which time a white precipitate formed. EPO <DP n="16"/>Dioxane was evaporated under reduced pressure. Water (400 ml.) was added and the product extracted with dichloromethane (3 x 400 ml_). The organic phase was dried (MgSO4) and concentrated in vacuo to afford endo-3-hydroxy-9-azabicyclo[3.3.1]nonane- 9-carboxylic acid tert-butyl ester (24.0 g, 0.10 mol, 83% from enαto-9-benzyl-9- azabicyclo[3.3.1]nonan-3-ol) as a pale yellow solid.
83% With sodium hydroxide; In 1,4-dioxane; water; at -15 - 20℃; for 4.16667h; Crude <strong>[504-12-1]endo-9-azabicyclo[3.3.1]nonan-3-ol</strong> (from Step c) was dissolved in a solution of dioxane (500 mL), water (187.5 mL) and 4N sodium hydroxide (aq.) (62.5 mL) and cooled to -15 C. under a nitrogen atmosphere. Di-tert-butyl dicarbonate (39.0 g, 0.18 mol) was added portionwise over 10 min, the reaction mixture allowed to warm to ambient temperature and stirring continued for 4 h during which time a white precipitate formed. Dioxane was evaporated under reduced pressure. Water (400 mL) was added and the product extracted with dichloromethane (3 400 mL). The organic phase was dried (MgSO4) and concentrated in vacuo to afford endo-3-hydroxy-9-azabicyclo[3.3.1]nonane-9-carboxylic acid tert-butyl ester (24.0 g, 0.10 mol, 83% from endo-9-benzyl-9-azabicyclo[3.3.1]nonan-3-ol) as a pale yellow solid.
  • 9
  • [ 70243-51-5 ]
  • [ 504-12-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; hydrogen;palladium 10% on activated carbon; In ethanol; water; at 40℃; for 48.0h; 10% Palladium on carbon (10% Pd/C) (5.0 g) was added to a solution of enαto-9-benzyl-9- azabicyclo[3.3.1]nonan-3-ol (27.0 g, 0.12 mol) in ethanol (500 ml.) and 5N aqueous hydrochloric acid (25 ml_). The mixture was stirred under a hydrogen atmosphere (3 bar) at 40 0C for 48 h. The mixture was then filtered through a pad of dicalite and the filtrate was evaporated in vacuo and remaining aqueous mixture azeotroped with toluene (2 x150 ml.) to yield crude endo-9-azabicyclo[3.3.1]nonan-3-ol as a pale yellow solid which was used directly in the next stage.
With hydrogen;palladium 10% on activated carbon; In ethanol; water; at 40℃; under 2250.23 Torr; for 48.0h; 10% Palladium on carbon (10% Pd/C) (5.0 g) was added to a solution of endo-9-benzyl-9-azabicyclo[3.3.1]nonan-3-ol (27.0 g, 0.12 mol) in ethanol (500 mL) and 5N aqueous hydrochloric acid (25 mL). The mixture was stirred under a hydrogen atmosphere (3 bar) at 40 C. for 48 h.The mixture was then filtered through a pad of dicalite and the filtrate was evaporated in vacuo and remaining aqueous mixture azeotroped with toluene (2 150 mL) to yield crude endo-9-azabicyclo[3.3.1]nonan-3-ol as a pale yellow solid which was used directly in the next stage.
  • 10
  • [ 4390-39-0 ]
  • [ 504-12-1 ]
  • [ 26651-94-5 ]
YieldReaction ConditionsOperation in experiment
With cis-RuCl2[dppb][Me-bima]; potassium tert-butylate; hydrogen; In butan-1-ol; at 25℃; under 7600.51 Torr; for 17.0h; Example 6 Preparation Examples of endo-9-azabicyclo[3.3.1]nonan-3-ol A reduction reaction of a 9-azabicyclo[3.3.1]nonan-3-one was conducted using a cis-RuCl2(dppb)(ammp) or a cis-RuCl2(Me-bima) under the conditions shown in Table 6. The results are shown in Table 6.
 

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