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

HRID 1463606Notes

Reaction equation

HRID 1463606 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-cbb47916ffe244c297aa87d8c9a26466
Source dataset
uspto-grants-1994_04
Patent number
US05300679

Reaction notes

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