Aluminium lithium hydride → HCID 70378321, compound

HRID 620330Notes

Reaction equation

HRID 620330 reaction equation
[CH2:1]([O:8][C:9]1[CH:26]=[CH:25][C:12]([C@@H:13]([C@@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][C:19]2=[O:24])[CH2:14][N+:15]([O-])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.O>O1CCCC1>[NH2:15][CH2:14][C@H:13]([C@@H:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C@@H:19]1[OH:24])[C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 21881883Oxolane--water (1/1)HCID 44191935HCID 44191935, compound

Product 1

HCID 70378321HCID 70378321, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 9.5 g of (-)-(S)-[(R)-4-(benzyloxy)-α-(nitromethyl)benzyl]cyclohexanone in 150 ml of dry tetrahydrofuran is added dropwise at room temperature while stirring to a suspension of 2.5 g (67.2 mmol) of lithium aluminium hydride in 80 ml of dry tetrahydrofuran under argon and the mixture is stirred at room temperature for 16 hours. The reaction mixture is treated with 20 ml of 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 3N sodium hydroxide solution and extracted with methylene chloride. The organic phase is washed with water, dried over magnesium sulphate and evaporated. There is obtained (+)-(1S)-cis-2-[(R)-α-(aminomethyl)-4-(benzyloxy)benzyl]cyclohexanol in the form of a colourless oil; [α]D20 =+14.7° (c=0.7, chloroform).

Workup

  1. filtrationthe separated precipitate is filtered off under suction
  2. washwhile washing with methylene chloride
  3. customthe filtrate is evaporated
  4. dissolutionThe residue is dissolved in ether
  5. extractionthe ethereal phase is extracted with 1N hydrochloric acid
  6. extractionextracted with methylene chloride
  7. washThe organic phase is washed with water
  8. dry with materialdried over magnesium sulphate
  9. customevaporated

Sources & evidence

ORD record
ord-1a50220835f442d6a610298cdc370065
Source dataset
uspto-grants-1989_04
Patent number
US04820734

Reaction notes

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