Aluminium lithium hydride → 9-(phenylmethyl)-3,9-Diazabicyclo[4.2.1]nonane

HRID 1986013Notes

Reaction equation

HRID 1986013 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:14]1[CH:20]2[CH2:21][CH2:22][CH:15]1[CH2:16][NH:17][C:18](=O)[CH2:19]2)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([N:14]1[CH:20]2[CH2:21][CH2:22][CH:15]1[CH2:16][NH:17][CH2:18][CH2:19]2)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 457927509-Benzyl-3,9-diazabicyclo[4.2.1]nonan-4-one

Product 1

HCID 220579069-(phenylmethyl)-3,9-Diazabicyclo[4.2.1]nonane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Neat LAH (0.4 g, 10.54 mmol) was added in small portions to a stirred solution of 9-benzyl-3,9-diazabicyclo[4.2.1]nonan-4-one (1.2 g, 5.21 mmol) in THF (40 ml) and the mixture was stirred under nitrogen overnight. Reaction mixture was cooled in ace bath and quenched by consecutive addition of water (0.4 ml), 15% NaOH (1.2 ml) and water (0.4 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-benzyl-3,9-diazabicyclo[4.2.1]nonane as a light yellow oil. LC/MS: m/e 217 (MH+).

Workup

  1. customReaction mixture
  2. temperaturewas cooled in ace bath
  3. customquenched by consecutive addition of water (0.4 ml), 15% NaOH (1.2 ml) and water (0.4 ml)
  4. stirringstirred for 30 min
  5. filtrationPrecipitated sodium aluminate was filtered off
  6. dry with materialthe filtrate was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-a5996a4f028844e8ba2214593e3e5825
Source dataset
uspto-grants-2009_06
Patent number
US07547690B2

Reaction notes

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