Aluminium lithium hydride → HCID 68552870, compound

HRID 1804856Notes

Reaction equation

HRID 1804856 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][C:14]([CH2:18][C:19](OCC)=[O:20])([OH:17])[CH2:13][CH2:12]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[N:11]1[CH2:16][CH2:15][C:14]([CH2:18][CH2:19][OH:20])([OH:17])[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68558837HCID 68558837, compound

Product 1

HCID 68552870HCID 68552870, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(1-(2,4-dichloro-5-methoxyphenyl)-4-hydroxypiperidin-4-yl)acetate (1 g, 2.76 mmol) in THF (10 mL) was added LiAlH4 (0.210 g, 5.52 mmol). The reaction mixture was stirred at RT for 2 h, quenched with minimum water and then treated with EtOAc and solid NaHCO3. The mixture was stirred and filtered. The filtrate was concentrated to give 1-(2,4-dichloro-5-methoxyphenyl)-4-(2-hydroxyethyl)piperidin-4-ol (0.62 g, 1.936 mmol, 70% yield) as a yellow oil.

Workup

  1. customquenched with minimum water
  2. additiontreated with EtOAc and solid NaHCO3
  3. stirringThe mixture was stirred
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ba40bf464dd44486b10929fd182a2f7f
Source dataset
uspto-grants-2013_01
Patent number
US08354432B2

Reaction notes

Loading…