(2S)-2-[(1R)-1-(4-chlorophenyl)-2-nitroethyl]cyclohexan-1-one → HCID 57108580, compound

HRID 620329Notes

Reaction equation

HRID 620329 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([C@@H:6]([C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]2=[O:17])[CH2:7][N+:8]([O-])=O)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.O>O1CCCC1>[NH2:8][CH2:7][C@H:6]([C@@H:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]1[OH:17])[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 11173578(2S)-2-[(1R)-1-(4-chlorophenyl)-2-nitroethyl]cyclohexan-1-oneHCID 21226445Aluminium lithium hydrideHCID 21881883Oxolane--water (1/1)

Product 1

HCID 57108580HCID 57108580, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4.55 g (16.1 mmol) of (-)-(2S)-[(R)-4-chloro-α-(nitromethyl)benzyl]cyclohexanone [prepared according to Helv. Chim. Acta 65, 1637 (1982)] in 80 ml of dry tetrahydrofuran is added dropwise at room temperature while stirring to a suspension of 1.5 g (40.4 mmol) of lithium aluminium hydride in 50 ml of dry tetrahydrofuran under argon. The reaction mixture is stirred at room temperature overnight, 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 hydrochlorid 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-chlorobenzyl]cyclohexanol in the form of a yellow oil ([α]D20 =+14.7°, c=0.6 in chloroform), which is processed as such.

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 hydrochlorid 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-5ea9d1b3b7184b13bc607bcf3fbc76b7
Source dataset
uspto-grants-1989_04
Patent number
US04820734

Reaction notes

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