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

HRID 973614Notes

Reaction equation

HRID 973614 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 2 N 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-5d0b95de6e20412a80fab9f9c4604ed5
Source dataset
uspto-grants-1991_11
Patent number
US05064819

Reaction notes

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