Trimethylsilyl iodide → HCID 14966680, compound

HRID 2226846Notes

Reaction equation

HRID 2226846 reaction equation
C([O:3][P:4]([CH:7]([N:12]1[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]1)[P:8](=[O:11])([OH:10])[OH:9])(=[O:6])[OH:5])C.C[Si](I)(C)C>C(Cl)(Cl)(Cl)Cl>[O:18]=[C:15]1[CH2:14][CH2:13][N:12]([CH:7]([P:8](=[O:9])([OH:10])[OH:11])[P:4](=[O:3])([OH:5])[OH:6])[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 54072221HCID 54072221, compound

Product 1

HCID 14966680HCID 14966680, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
27.5 °C

Procedure

7.7 g of 4-oxopiperidinomethylene bisphosphonic acid ethyl ester and 12 ml of trimethylsilyl iodide (specific gravity: 1.41) were stirred at 0° C. for 30 minutes in 120 ml of CCl4. Then, the reaction solution was distilled under reduced pressure. To the residue, 50 ml of water and 200 ml of CH3OH were added, and the mixture was stirred at a temperature of from 25 to 30° C. for 5 hours. The reaction solution was distilled, and the residue was purified by silica gel column chromatography (chloroform/methanol=9/1) to give 2.0 g (yield: 37%) 4-oxopiperidinomethylene bisphosphonic acid.

Workup

  1. distillationThen, the reaction solution was distilled under reduced pressure
  2. additionTo the residue, 50 ml of water and 200 ml of CH3OH were added
  3. distillationThe reaction solution was distilled
  4. customthe residue was purified by silica gel column chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-16ab05040aa24329b29022e3e5f10d85
Source dataset
uspto-grants-1994_09
Patent number
US05350743

Reaction notes

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