Sodium bis(2-methoxyethoxy)aluminiumhydride → 1,2,2a,3,4,5-Hexahydroacenaphthylen-1-amine

HRID 331230Notes

Reaction equation

HRID 331230 reaction equation
[C:1]1(=[N:13]O)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][CH:3]3[CH2:2]1.[H-].[H-].COCCO[Al+]OCCOC.[Na+]>C1(C)C=CC=CC=1>[CH:1]1([NH2:13])[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][CH:3]3[CH2:2]1

Participants

4

Reactant 2

HCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 86641629HCID 86641629, compound

Product 1

HCID 638213741,2,2a,3,4,5-Hexahydroacenaphthylen-1-amineYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To 2a,3,4,5-tetrahydro-2H-acenaphthylen-1-one oxime (7.00 g) was added a solution (about 65%, 50 ml) of sodium bis(2-methoxyethoxy)aluminum dihydride in toluene, and the mixture was stirred with heating at 80° C. for 2 hr. After cooling to room temperature, the reaction mixture was poured into ice water, and the mixture was extracted with chloroform. After concentration under reduced pressure, the residue was extracted with 1N hydrochloric acid. The aqueous layer was alkalified with potassium carbonate, and extracted with chloroform. The extract was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure to give the title compound (5.34 g, 83%).

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with chloroform
  3. concentrationAfter concentration under reduced pressure
  4. extractionthe residue was extracted with 1N hydrochloric acid
  5. extractionextracted with chloroform
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-691ab29fc7484478b86179744f67ea7d
Source dataset
uspto-grants-2014_11
Patent number
US08877779B2

Reaction notes

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