Sodium hydride → HCID 67194178, compound

HRID 1295584Notes

Reaction equation

HRID 1295584 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[CH2:7]P(=O)(OCC)OCC)([O-:3])=[O:2].O=[C:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1.[H-].[Na+]>O1CCCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[CH:7]=[C:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 13675396Diethyl 3-Nitrobenzylphosphonate

Product 1

HCID 67194178HCID 67194178, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of diethyl (3-nitrobenzyl)phosphonate (8.4 g, 0.031 mol) and tert-butyl 4-oxopiperidine-1-carboxylate (6.12 g, 0.031 mol) in dry tetrahydrofuran (120 mL) was treated with a 60% suspension of sodium hydride in oil (1.36 g, 0.034 mmol). The resulting mixture was stirred at room temperature for 4 h, then partitioned between dichloromethane (500 mL) and water (500 mL). The organic extract was dried (Na2SO4) and evaporated in vacuo to give the title compound (9.86 g, 100%) as a solid.

Workup

  1. custompartitioned between dichloromethane (500 mL) and water (500 mL)
  2. extractionThe organic extract
  3. dry with materialwas dried (Na2SO4)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-f42a483edef441828773a978019cf7b0
Source dataset
uspto-grants-2007_07
Patent number
US07244726B2

Reaction notes

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