Trimethylsilyl iodide → HCID 14850749, compound

HRID 1164850Notes

Reaction equation

HRID 1164850 reaction equation
C([O:3][P:4]([CH2:9][C@H:10]1[CH2:15][CH2:14][NH:13][C@@H:12]([C:16]([NH2:18])=[O:17])[CH2:11]1)([O:6]CC)=[O:5])C.C[Si](I)(C)C>C(Cl)Cl>[P:4]([CH2:9][C@H:10]1[CH2:15][CH2:14][NH:13][C@@H:12]([C:16]([NH2:18])=[O:17])[CH2:11]1)([OH:5])([OH:6])=[O:3]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 14541441HCID 14541441, compound

Product 1

HCID 14850749HCID 14850749, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 278 mg of cis-4-diethylphosphonomethyl-2-piperidinecarboxamide in 5 ml of methylene chloride to which is added 0.43 ml of trimethylsilyl iodine is stirred at room temperature for 16 hours. The mixture is evaporated to dryness, the residue is dissolved in water, and the solution is evaporated to dryness. A solution of the resulting solid in ethanol is treated with 0.21 ml of propylene oxide to yield cis-4-phosphonomethyl-2-piperidinecarboxamide, m.p. 295°-298° dec.

Workup

  1. customThe mixture is evaporated to dryness
  2. dissolutionthe residue is dissolved in water
  3. customthe solution is evaporated to dryness
  4. additionA solution of the resulting solid in ethanol is treated with 0.21 ml of propylene oxide

Sources & evidence

ORD record
ord-cedc666f7e934f94a3149254f84e6e85
Source dataset
uspto-grants-1990_03
Patent number
US04906621

Reaction notes

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