Bromotrimethylsilane → 3-Aminooctane-1,1-bisphosphonic acid, triammonium salt

HRID 1977

Reaction equation

HRID 1977 reaction equation
[NH2:1][CH:2]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:3][CH:4]([P:13]([O:18]CC)(=[O:17])[O:14]CC)[P:5]([O:10]CC)(=[O:9])[O:6]CC.Br[Si](C)(C)C>ClCCl>[NH4+:1].[NH4+:1].[NH4+:1].[NH2:1][CH:2]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:3][CH:4]([P:5]([O-:10])(=[O:6])[OH:9])[P:13]([O-:18])(=[O:14])[O-:17]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 19689051Tetraethyl 3-aminooctane-1,1-bisphosphonate

Product 1

HCID 1317205653-Aminooctane-1,1-bisphosphonic acid, triammonium saltYield 419.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tetraethyl 3-aminooctane-1,1-bisphosphonate (0.45 g, 1.12 mmol) in dry dichloromethane (1.1 mL) was added bromotrimethylsilane (1.05 mL, 7.85 mmol) via syringe. After 18 hours, the mixture was concentrated under vacuum. To the residue was added 3N NH4OH (8 mL) which was stirred for 30 minutes at room temperature. The solvent was removed in vacuo and the residue concentrated from methanol (2 mL) to give 0.40 g of 3-aminooctane-1,1-bisphosphonic acid, triammonium salt as a white powder.

Workup

  1. concentrationthe mixture was concentrated under vacuum
  2. additionTo the residue was added 3N NH4OH (8 mL) which
  3. customThe solvent was removed in vacuo
  4. concentrationthe residue concentrated from methanol (2 mL)

Sources & evidence

ORD record
ord-66715e3038e443c89124069570855fa8
Source dataset
uspto-grants-1998_03
Patent number
US05728650

Linked notes

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