Hydrochloric Acid → HCID 53983165, compound

HRID 620320Notes

Reaction equation

HRID 620320 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([C@@H:6]([CH: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.Cl>O1CCCC1.C(OC(C)C)(C)C>[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]([F:1])=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 21881883Oxolane--water (1/1)HCID 53951296HCID 53951296, compound

Product 1

HCID 53983165HCID 53983165, compound

Reagents, catalysts & solvents 2

HCID 7914Diisopropyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 105 g (0.4 mol) of rac-(2S*)-2-[(R*)-4-fluoro-α-(nitromethyl)benzyl]cyclohexanone in 1 l of dry tetrahydrofuran is added dropwise while stirring to a suspension of 38 g (1 mol) of lithium aluminum hydride in 500 ml of dry tetrahydrofuran under argon so that the temperature does not exceed 50°. The reaction mixture is stirred at 50° for 15 hours, cooled and then treated with tetrahydrofuran/water (1:1). The separated precipitate is filtered off under suction while washing with methylene chloride and the filtrate is distilled. The oil obtained is treated with 3N hydrochloric acid, extracted twice with 500 ml of ether each time, the aqueous phase is made alkaline with ammonia and extracted with ether. The organic phase is washed with water, dried over magnesium sulphate and evaporated. The oil obtained is dissolved in 250 ml of isopropyl ether, whereupon the solution is left to stand in a refrigerator overnight for crystallization. There is obtained rac-(1S*)-cis-2-[(R*)-α-(aminomethyl)-4-fluorobenzyl]cyclohexanol in the form of colourless crystals of m.p. 75°-76°. The rac-(1S*)-cis-2-[(R*)-α-(aminomethyl)-4-fluorobenzyl]cyclohexanol hydrochloride prepared in the usual manner is recrystallized from ethanol/ether; there are obtained colourless crystals of m.p. 233°-234°.

Workup

  1. customdoes not exceed 50°
  2. temperaturecooled
  3. filtrationThe separated precipitate is filtered off under suction
  4. washwhile washing with methylene chloride
  5. distillationthe filtrate is distilled
  6. customThe oil obtained
  7. extractionextracted twice with 500 ml of ether each time
  8. extractionextracted with ether
  9. washThe organic phase is washed with water
  10. dry with materialdried over magnesium sulphate
  11. customevaporated
  12. customThe oil obtained
  13. waitis left
  14. customto stand in a refrigerator overnight for crystallization

Sources & evidence

ORD record
ord-1df521aa691e41459d54d6028d57c8da
Source dataset
uspto-grants-1989_04
Patent number
US04820734

Reaction notes

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