Ammonium formate → Tetraethyl 3-aminooctane-1,1-bisphosphonate

HRID 1976

Reaction equation

HRID 1976 reaction equation
[N+:1]([CH:4]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:5][CH:6]([P:15]([O:20][CH2:21][CH3:22])(=[O:19])[O:16][CH2:17][CH3:18])[P:7]([O:12][CH2:13][CH3:14])(=[O:11])[O:8][CH2:9][CH3:10])([O-])=O.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:1][CH:4]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:5][CH:6]([P:15]([O:20][CH2:21][CH3:22])(=[O:19])[O:16][CH2:17][CH3:18])[P:7]([O:8][CH2:9][CH3:10])(=[O:11])[O:12][CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 2723923Ammonium formate2×HCID 19689057Tetraethyl 3-nitrooctane-1,1-bisphosphonate

Product 1

HCID 19689051Tetraethyl 3-aminooctane-1,1-bisphosphonateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

To a stirred solution of tetraethyl 3-nitrooctane-1,1-bisphosphonate (0.70 g, 1.62 mmol) in methanol (4 mL) was added ammonium formate (0.45 g, 6.9 mmol) and 10% palladium on carbon (0.070 g). After 24 hours, more 10% palladium on carbon (0.035 g) and ammonium formate (0.45 g, 6.9 mmol) were added. After stirring for a total of 4 days, the reaction mixture was filtered, rinsing the residue with methanol, and concentrated. The residue was taken up in brine (5 mL) and extracted with dichloromethane (4×15 mL), dried (Na2SO4) and concentrated to give the title compound (0.60 g, 95%) as an oil.

Workup

  1. filtrationthe reaction mixture was filtered
  2. washrinsing the residue with methanol
  3. concentrationconcentrated
  4. extractionextracted with dichloromethane (4×15 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6f9159e7c4774638b827a4db2641898a
Source dataset
uspto-grants-1998_03
Patent number
US05728650

Linked notes

Loading…