Sodium Hydroxide → (1-Isopropylpiperidin-4-yl)methanol

HRID 1784887Notes

Reaction equation

HRID 1784887 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]([N:10]1[CH2:15][CH2:14][CH:13]([C:16](OCC)=[O:17])[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][OH:17])[CH2:12][CH2:11]1)([CH3:9])[CH3:8]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 19900430Ethyl 1-isopropylpiperidine-4-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 11147855(1-Isopropylpiperidin-4-yl)methanolYield 105.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-50 °C

Procedure

Lithium aluminum hydride (500 mg) was suspended in 40 ml of tetrahydrofuran, a solution of 3.55 g of ethyl 1-isopropylpiperidine-4-carboxylate in 10 ml of tetrahydrofuran was added thereto at −50° C. and the mixture was stirred for 2.5 hours from under ice-cooling to at room temperature. To this were added 0.5 ml of water, 0.5 ml of a 2N aqueous solution of sodium hydroxide, 1.5 ml of water and anhydrous magnesium sulfate under ice-cooling, the resulting precipitate was removed by filtration and the solvent was evaporated in vacuo to give 2.96 g of (1-isopropyl-4-piperidyl)methanol.

Workup

  1. temperaturecooling to at room temperature
  2. temperaturecooling
  3. customthe resulting precipitate was removed by filtration
  4. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-9934eafc6bc044718d676c4a1f11e389
Source dataset
uspto-grants-2009_03
Patent number
US07504417B2

Reaction notes

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