Reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][N:8]1[CH:14]2[CH2:15][CH2:16][CH:9]1[CH2:10][NH:11][C:12](=O)[CH2:13]2.O>C1COCC1.ClCCl>[CH3:7][N:8]1[CH:14]2[CH2:15][CH2:16][CH:9]1[CH2:10][NH:11][CH2:12][CH2:13]2Participants
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of LiAlH4 (0.61 g) in anhydrous THF (30 ml), cooled at 0° C., and kept under an argon inert atmosphere, a solution in THF of 9-methyl-3,9-diazabicyclo[4.2.1]nonan-4-one obtained in example 1 is dropwise added (1.00: of compound in 10 ml of THF). The obtained mixture is heated at reflux for 48 hours and then cooled at 0° C. Then water (3 ml) is slowly added to the mixture. After water addition, the mixture is kept under stirring for 1:0 minutes. A precipitate is formed, that at the end is filtered under vacuum and washed with dichloromethane. The obtained filtrate is evaporated obtaining an oil which is dissolved in dichloromethane. The obtained solution is then anhydrified on sodium sulphate and the solvent evaporated. The residual oil is distilled (45-50° C./0.1 mmHg) to give 0.63 g of 9-methyl-3,9-diazabicyclo[4.2.1]nonane (2a) as a colourless oil.
Workup
- temperatureThe obtained mixture is heated
- temperatureat reflux for 48 hours
- temperaturecooled at 0° C
- custom0 minutes
- customA precipitate is formed, that at the end
- filtrationis filtered under vacuum
- washwashed with dichloromethane
- customThe obtained filtrate is evaporated
- customobtaining an oil which
- customthe solvent evaporated
- distillationThe residual oil is distilled (45-50° C./0.1 mmHg)
Sources & evidence
- ORD record
- ord-1182d64edc7f4c0bab5e87d3d759b2fd
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399457B2
Linked notes
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