Hydrochloric Acid → HCID 86742917, compound

HRID 620317Notes

Reaction equation

HRID 620317 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C@@H:4]([CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=[O:15])[CH2:5][N+:6]([O-])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)C.Cl>O1CCCC1.O1CCCC1.O>[ClH:1].[NH2:6][CH2:5][C@H:4]([C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[OH:15])[C:3]1[CH:16]=[CH:17][CH:18]=[CH:19][C:2]=1[Cl:1]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 21226445Aluminium lithium hydrideHCID 53961776HCID 53961776, compound

Product 1

HCID 86742917HCID 86742917, compound

Reagents, catalysts & solvents 2

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

Procedure

A solution of 56.3 g (0.2 mol) of rac-(2S*)-2-[(R*)-2-chloro-α-(nitromethyl)benzyl]cyclohexanone in 500 ml of dry tetrahydrofuran is added dropwise while stirring to a suspension of 18.9 g (0.5 mol) of lithium aluminium hydride in 500 ml of dry tetrahydrofuran under argon so that the temperature does not exceed 50°. The reaction mixture is then stirred at 50° for a further 15 hours. After cooling the mixture is treated first with 50 ml of ethanol and subsequently with tetrahydrofuran/water (1:1), the separated precipitate is filtered off under suction while washing with methylene chloride and the filtrate is evaporated. The oily residue obtained is treated with 3N hydrochloric acid, whereupon the mixture is 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 methylene chloride each time. The organic phase is washed with water, dried over magnesium sulphate and evaporated. The crude product is obtained in the form of a yellow oil; it is converted into the hydrochloride in the usual manner. After repeated recrystallization from methylene chloride/methanol there is obtained rac-(1S*)-cis-2-[(R*)-α-(aminomethyl)-2-chlorobenzyl]cyclohexanol hydrochloride of m.p. 278°-280°.

Workup

  1. customdoes not exceed 50°
  2. temperatureAfter cooling the mixture
  3. filtrationthe separated precipitate is filtered off under suction
  4. washwhile washing with methylene chloride
  5. customthe filtrate is evaporated
  6. customThe oily residue obtained
  7. extractionis extracted twice with 250 ml of ether each time
  8. extractionextracted twice with 500 ml of methylene chloride each time
  9. washThe organic phase is washed with water
  10. dry with materialdried over magnesium sulphate
  11. customevaporated
  12. customThe crude product is obtained in the form of a yellow oil
  13. customrecrystallization from methylene chloride/methanol there

Sources & evidence

ORD record
ord-4a23e014312e43d5a0f94b744b936e43
Source dataset
uspto-grants-1989_04
Patent number
US04820734

Reaction notes

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