Sodium hydride → HCID 69036432, compound

HRID 1985733Notes

Reaction equation

HRID 1985733 reaction equation
[H-].[Na+].C(OP([CH2:11][C:12]#[N:13])(=O)OCC)C.[CH2:14]([O:16][C:17]([N:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1)=[O:18])[CH3:15]>O1CCCC1>[CH2:14]([O:16][C:17]([N:19]1[CH2:24][CH2:23][C:22](=[CH:11][C:12]#[N:13])[CH2:21][CH2:20]1)=[O:18])[CH3:15]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 34767Ethyl 4-oxo-1-piperidinecarboxylateHCID 75676Diethyl (cyanomethyl)phosphonate

Product 1

HCID 69036432HCID 69036432, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 12.85 g (321.28 mmol) of sodium hydride (60% suspension in mineral oil) in 500 ml of anhydrous tetrahydrofuran at 0° C., was added 56.91 g (321.28 mmol) of diethyl-(cyanomethyl)-phosphonate over a 10-min period. The reaction mixture was stirred for 2 h at room temperature and then 44.05 g (292.07 mmol) of 4-oxo-piperidine-1-carboxylic acid ethyl ester in 230 ml of anhydrous tetrahydrofuran was added dropwise over 30 min. The resulting mixture was stirred at room temperature for 16 h.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 16 h.

Sources & evidence

ORD record
ord-cf40979b64324455a682697ec9f2d6cc
Source dataset
uspto-grants-2009_06
Patent number
US07547705B2

Reaction notes

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