Aluminium lithium hydride → HCID 9860329, compound

HRID 227570Notes

Reaction equation

HRID 227570 reaction equation
C[O:2][C:3]([C@H:5]1[C@@H:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[CH2:9][CH2:8][N:7]([CH3:19])[CH2:6]1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH3:19][N:7]1[CH2:8][CH2:9][C@H:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)[C@H:5]([CH2:3][OH:2])[CH2:6]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 44429174(3S,4S)-methyl 4-(3,4-dichlorophenyl)-1-methylpiperidine-3-carboxylate

Product 1

HCID 9860329HCID 9860329, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

A solution of (1) (5.0 g, 17 mmol) in tetrahydrofuran (50 ml) at −50° C. was added LiAlH4 (0.50 g, 13 mmol). Stirred at −30° C. for three hours, then quenched by addition of water and evaporated to a solid. The residue was dissolved in dichloromethane, dried with magnesium sulfate and evaporated to dryness. Yield 4.6 g of (3) (100%). Mp. 127-129° C.

Workup

  1. customquenched by addition of water
  2. customevaporated to a solid
  3. dissolutionThe residue was dissolved in dichloromethane
  4. dry with materialdried with magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-f6e2cd16ba6f44729086ded32bdbd24e
Source dataset
uspto-grants-2009_07
Patent number
US07560562B2

Reaction notes

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