Sodium Hydroxide → HCID 45096503, compound

HRID 131275Notes

Reaction equation

HRID 131275 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][C:17](OCC)=[O:18])[CH2:12][CH2:11]1)([CH3:9])[CH3:8].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.O>[CH:7]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][OH:18])[CH2:12][CH2:11]1)([CH3:9])[CH3:8]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 57678052HCID 57678052, compound

Product 1

HCID 45096503HCID 45096503, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

Under argon gas atmosphere, lithium aluminum hydride (1.19 g) is suspended in tetrahydrofuran (50 mL) and thereto is added dropwise a solution of ethyl (1-isopropylpiperidin-4-yl)acetate (compound obtained in Reference Example 93(1), 6.43 g) in tetrahydrofuran (50 mL) over a period of 15 minutes under ice-cooling. The mixture is stirred at room temperature for 1.5 hours. To the reaction mixture is added successively water (1.2 mL), 2N sodium hydroxide solution (2.4 mL), and water (2.4 mL) under ice-cooling. The mixture is stirred at room temperature for 2 hours. After addition of magnesium sulfate, the reaction mixture is stirred for 10 minutes and filtered. The filtrate is concentrated in vacuo and the residue is purified by flash column chromatography on NH-silica gel (Solvent; n-hexane:ethyl acetate=1:1) to give 2-(1-isopropylpiperidin-4-yl)ethanol (5.09 g, yield; 99%) as a colorless oil. MS (APCI) m/z: 172 [M+H]+

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringThe mixture is stirred at room temperature for 2 hours
  4. stirringthe reaction mixture is stirred for 10 minutes
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated in vacuo
  7. customthe residue is purified by flash column chromatography on NH-silica gel (Solvent; n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-87123cae46304c3cbe0fb8ceef4067d3
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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