Potassium Carbonate → HCID 86742918, compound

HRID 620321Notes

Reaction equation

HRID 620321 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[C@@H:6]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C:12]1=[O:17])[CH2:7][N+:8]([O-])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(=O)([O-])[O-].[K+].[K+].[C:33]([O-:38])(=[O:37])[C:34]([O-:36])=[O:35]>O1CCCC1.O1CCCC1.O.C(O)C>[C:33]([OH:38])(=[O:37])[C:34]([OH:36])=[O:35].[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:18]=[CH:19][CH:20]=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 71081OxalateHCID 21226445Aluminium lithium hydrideHCID 54187170HCID 54187170, compound

Product 1

HCID 86742918HCID 86742918, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 41.6 g (0.15 mol) of rac-(2S*)-2-[(R*)-3-methoxy-α-(nitromethyl)benzyl]cyclohexanone in 400 ml of dry tetrahydrofuran is added dropwise to a suspension of 14.2 g (0.38 mol) of lithium aluminum hydride in 400 ml of dry tetrahydrofuran under argon. The reaction mixture is then heated to boiling under reflux for 4 hours, treated, after cooling, firstly with 50 ml of ethanol, and subsequently with tetrahydrofuran/water (1:1), treated with 80 g of potassium carbonate and stirred for 30 minutes. The separated precipitate is filtered off under suction while washing with methylene chloride and the filtrate is evaporated. The residue is treated with 3N hydrochloric acid and extracted twice with 250 ml of ether each time. The aqueous phase is made alkaline with 3N sodium hydroxide solution and extracted twice with 500 ml of ether each time. The organic phase is washed twice with 50 ml of sodium chloride solution each time, dried over magnesium sulphate and evaporated. The crude product obtained as a yellowish oil is converted into the oxalate which is recrystallized from acetone. The rac-(1S*)-cis-2-[(R*)-α-(aminomethyl)-3-methoxybenzyl]cyclohexanol oxalate (2:1) obtained melts at 210°212°.

Workup

  1. temperatureThe reaction mixture is then heated
  2. temperatureunder reflux for 4 hours
  3. additiontreated
  4. filtrationThe separated precipitate is filtered off under suction
  5. washwhile washing with methylene chloride
  6. customthe filtrate is evaporated
  7. additionThe residue is treated with 3N hydrochloric acid
  8. extractionextracted twice with 250 ml of ether each time
  9. extractionextracted twice with 500 ml of ether each time
  10. washThe organic phase is washed twice with 50 ml of sodium chloride solution each time
  11. dry with materialdried over magnesium sulphate
  12. customevaporated
  13. customThe crude product obtained as a yellowish oil
  14. customis recrystallized from acetone

Sources & evidence

ORD record
ord-f0e6abe440b147609d6cbc9697d1032f
Source dataset
uspto-grants-1989_04
Patent number
US04820734

Reaction notes

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