Aluminium lithium hydride → HCID 54216347, compound

HRID 620328Notes

Reaction equation

HRID 620328 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@H:12]2[OH: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 21226445Aluminium lithium hydrideHCID 21881883Oxolane--water (1/1)HCID 54286268HCID 54286268, compound

Product 1

HCID 54216347HCID 54216347, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1.9 g (6.7 mmol) of rac-(1R*)-trans-2-[(R*)-4-chloro-α-(nitromethyl)benzyl]cyclohexanol in 30 ml of dry tetrahydrofuran is added dropwise while stirring to a suspension of 1 g of lithium aluminium hydride in 60 ml of dry tetrahydrofuran under argon, whereupon the mixture is stirred at 50° overnight. After cooling the reaction mixture is treated with tetrahydrofuran/water (1:1), the precipitate is filtered off under suction, the filtrate is evaporated, the residue is treated with water and extracted with ether. The rac-(1R*)-trans-2-[(R*)-α-(aminomethyl)-4-chlorobenzyl]cyclohexanol obtained is a colourless oil and is processed directly.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. filtrationthe precipitate is filtered off under suction
  3. customthe filtrate is evaporated
  4. additionthe residue is treated with water
  5. extractionextracted with ether

Sources & evidence

ORD record
ord-651c93c85df04da8a616cfc218a15233
Source dataset
uspto-grants-1989_04
Patent number
US04820734

Reaction notes

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