Water → 5-(Hydroxymethyl)piperidin-2-one

HRID 467233Notes

Reaction equation

HRID 467233 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([CH:12]1[CH2:17][NH:16][C:15](=[O:18])[CH2:14][CH2:13]1)=O)C.O.[OH-].[Na+]>C1COCC1>[OH:9][CH2:10][CH:12]1[CH2:17][NH:16][C:15](=[O:18])[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 15386078Ethyl 6-oxopiperidine-3-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 153860795-(Hydroxymethyl)piperidin-2-oneYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Solid lithium aluminum hydride (3.5 g) was added slowly to a solution of 15.0 g 5-ethoxycarbonyl-2-piperidone in 350 ml THF at -4° C. After stirring for 1 hour under a nitrogen atmosphere, the reaction was decomposed by dropwise addition of 3.5 ml water, 3.5 ml 5N NaOH and 10.5 ml water. The mixture was filtered and the granular precipitate washed with 100 ml THF. Evaporation of the combined filtrate and washings provided 6.0 g of the title compound: MS m/z 130 (M+ +1), 129 (M+), 128 (M+ -1) 101, 73, 56; 90-MHz 1H NMR (CDCl3) δ1.42-1.60 (m, 1 H), 1.60-2.05 (m, 2 H), 2.10-2.47 (m, 2 H), 3.05 (t, J=9 Hz, 1 H), 3.21-3.58 (m, 4 H), 6.85 (s, 1 H).

Workup

  1. filtrationThe mixture was filtered
  2. washthe granular precipitate washed with 100 ml THF
  3. customEvaporation of the combined filtrate and washings

Sources & evidence

ORD record
ord-fd78a5cfeaeb4d2eb1c3be4a461616bc
Source dataset
uspto-grants-1992_10
Patent number
US05159079

Reaction notes

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