Hydrochloric Acid → Ethyl (3-aminobutyl)(diethoxymethyl)phosphinate

HRID 2050706Notes

Reaction equation

HRID 2050706 reaction equation
O=[C:2]([CH3:17])[CH2:3][CH2:4][P:5]([CH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])(=[O:9])[O:6][CH2:7][CH3:8].C([O-])(=O)C.[NH4+].C([BH3-])#[N:24].[Na+].Cl>CO>[NH2:24][CH:2]([CH3:17])[CH2:3][CH2:4][P:5]([CH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])(=[O:9])[O:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 14362820Ethyl 3-oxobutyl(diethoxymethyl)phosphinate

Product 1

HCID 14362822Ethyl (3-aminobutyl)(diethoxymethyl)phosphinate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1.0 g of ethyl 3-oxobutyl(diethoxymethyl)phosphinate 2.85 g of ammonium acetate and 0.16 g of sodium cyanoborohydride in 20 ml of methanol is stirred for 2.5 hours. After standing overnight, the pH is adjusted to pH 5,6 with 2N hydrochloric acid. The mixture is then evaporated to dryness. 20 ml of water are added and the mixture is washed 3 times with 20 ml of diethyl ether. The aqueous layer is adjusted to pH 12 with potassium hydroxide and extracted 4 times with 25 ml of chloroform. The organic layers are combined, dried, filtered and evaporated to dryness yielding ethyl 3-aminobutyl(diethoxymethyl)phosphinate, 31P-NMR spectrum: δ=+46.0 ppm (CDCl3).

Workup

  1. waitAfter standing overnight
  2. customThe mixture is then evaporated to dryness
  3. addition20 ml of water are added
  4. washthe mixture is washed 3 times with 20 ml of diethyl ether
  5. extractionextracted 4 times with 25 ml of chloroform
  6. customdried
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-375ba7ae7fb84b65a95cadbff64cb23f
Source dataset
uspto-grants-1991_05
Patent number
US05013863

Reaction notes

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