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

HRID 1986012

반응식

HRID 1986012 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ef9ca1c21b2a42caabcb3d2d96412e3b
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07547690B2

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