Aluminium lithium hydride → HCID 54302517, compound

HRID 620331Notes

Reaction equation

HRID 620331 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH:6]([CH:11]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]2=[O:19])[CH2:7][N+:8]([O-])=O)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH2:8][CH2:7][C@H:6]([CH:11]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[OH:19])[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54011700HCID 54011700, compound

Product 1

HCID 54302517HCID 54302517, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 7.4 g (23.9 mmol) of rac-(2S*)-2-[4-chloro-α-(nitromethyl)benzyl]cyclooctanone in 100 ml of dry tetrahydrofuran is added dropwise at 40° while stirring to a suspension of 2.3 g (59.7 mmol) of lithium aluminium hydride in 75 ml of dry tetrahydrofuran under argon and the mixture is stirred under reflux temperature overnight. The mixture is cooled, excess lithium aluminium hydride is destroyed with tetrahydrofuran/water (1:1), the separated precipitate is filtered off under suction while washing with methylene chloride and the filtrate is evaporated. The residue is dissolved in ether, the ethereal phase is extracted with 1N hydrochloric acid, the acidic phase is made alkaline with conc. ammonia and extracted with methylene chloride. The organic phase is washed with water, dried over magnesium sulphate and evaporated. After crystallization from methylene chloride/isopropyl ether there is obtained rac-(2S*)-2-[(R*)-α-(aminomethyl)-4-chlorobenzyl]cyclooctanol in the form of colourless crystals of m.p. 110°-111°.

Workup

  1. temperatureunder reflux temperature overnight
  2. temperatureThe mixture is cooled
  3. customexcess lithium aluminium hydride is destroyed with tetrahydrofuran/water (1:1)
  4. filtrationthe separated precipitate is filtered off under suction
  5. washwhile washing with methylene chloride
  6. customthe filtrate is evaporated
  7. dissolutionThe residue is dissolved in ether
  8. extractionthe ethereal phase is extracted with 1N hydrochloric acid
  9. extractionextracted with methylene chloride
  10. washThe organic phase is washed with water
  11. dry with materialdried over magnesium sulphate
  12. customevaporated
  13. customAfter crystallization from methylene chloride/isopropyl ether there

Sources & evidence

ORD record
ord-8a3908fbc6324f24839052329355e900
Source dataset
uspto-grants-1989_04
Patent number
US04820734

Reaction notes

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