9-Methyl-3,9-diazabicyclo(4.2.1)nonan-4-one → 9-Methyl-3,9-diazabicyclo[4.2.1]nonane

HRID 1986012

Reaction equation

HRID 1986012 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>C1COCC1>[CH3:7][N:8]1[CH:14]2[CH2:15][CH2:16][CH:9]1[CH2:10][NH:11][CH2:12][CH2:13]2

Participants

4

Reactant 2

HCID 5574669-Methyl-3,9-diazabicyclo(4.2.1)nonan-4-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 139737309-Methyl-3,9-diazabicyclo[4.2.1]nonane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Neat LAH (0.5 g, 13.17 mmol) was added in small portions to a stirred solution of 9-methyl-3,9-diazabicyclo[4.2.1]nonan-4-one (1.0 g, 6.48 mmol) in THF (40 ml) and the mixture was heated at reflux under nitrogen for 3-4 h. Reaction mixture was cooled in ace bath and quenched by consecutive addition of water (0.5 ml), 15% NaOH (1.5 ml) and water (0.5 ml) and then stirred for 30 min. Precipitated sodium aluminate was filtered off and the filtrate was dried over MgSO4, filtered and evaporated to dryness to afford 9-methyl-3,9-diazabicyclo[4.2.1]nonane as a light yellow oil. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.08-1.67 (m, 4H) 1.74-1.92 (m, 1H) 2.01-2.31 (m, 2H) 2.41-2.46 (m, 3H) 2.66 (dd, J=13.09, 2.01 Hz, 1H) 2.77-3.00 (m,2H) 3.07-3.36 (m, 2H) 3.50-4.06 (m, 1H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux under nitrogen for 3-4 h
  3. customReaction mixture
  4. temperaturewas cooled in ace bath
  5. customquenched by consecutive addition of water (0.5 ml), 15% NaOH (1.5 ml) and water (0.5 ml)
  6. filtrationPrecipitated sodium aluminate was filtered off
  7. dry with materialthe filtrate was dried over MgSO4
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-ef9ca1c21b2a42caabcb3d2d96412e3b
Source dataset
uspto-grants-2009_06
Patent number
US07547690B2

Linked notes

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