Water → 4-(2-Methoxyethyl)piperidine

HRID 1282010Notes

Reaction equation

HRID 1282010 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OC([N:14]1[CH2:19][CH2:18][CH:17]([CH2:20][C:21]([O:23][CH3:24])=O)[CH2:16][CH2:15]1)=O)(C)(C)C.O.[OH-].[Na+]>C1COCC1.CCOCC>[CH3:24][O:23][CH2:21][CH2:20][CH:17]1[CH2:18][CH2:19][NH:14][CH2:15][CH2:16]1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 1514280tert-Butyl 4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 151727544-(2-Methoxyethyl)piperidine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5 g (696.6 mmol) of LiAlH4 in 800 mL of THF at rt was carefully added 30 g (232.2 mmol) of 1-t-butoxycarbonyl-4-(methoxycarbonyl methyl)piperidine and the reaction mixture was stirred at rt for 24 h. To the reaction mixture was slowly added 30 mL of H2O over a period of 2 h, followed by 30 mL of a 15% NaOH solution and 30 mL of H2O. The mixture was diluted with ether, filtered, and the solids were triturated several times with ethyl acetate. The combined organic fractions were concentrated to give the title compound.

Workup

  1. customat rt
  2. customof 2 h
  3. filtrationfiltered
  4. customthe solids were triturated several times with ethyl acetate
  5. concentrationThe combined organic fractions were concentrated

Sources & evidence

ORD record
ord-d676f36357b4425c96f3a5eed0800fd7
Source dataset
uspto-grants-2002_09
Patent number
US06455548B2

Reaction notes

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