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

HRID 5171Notes

Reaction equation

HRID 5171 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

To a solution of 8.0 g of ethyl 3-oxobutyl(diethoxymethyl)phosphinate in 100 ml of methanol is added 22.8 g of ammonium acetate and 1.3 g of sodium cyanoborohydride. The mixture is stirred under an atmosphere of nitrogen at room temperature for a period of 2.5 h, and then left to stand overnight. The mixture is then acidified to pH 2 with the requisite amount of dilute hydrochloric acid and the methanol is evaporated under reduced pressure. The crude product is dissolved in 25 ml of water, washed twice with 20 ml of diethyl ether and the aqueous phase is then made alkaline to pH 12 with potassium hydroxide. The solution is then saturated with sodium chloride and extracted with 3×25 ml of dichloromethane. The organic phase is dried over magnesium sulphate, filtered and evaporated under reduced pressure and the crude product distilled to give ethyl 3-aminobutyl(diethoxymethyl)phosphinate, b.p. 150° C./0.01 mbar, 31P=+46.1 ppm (CDCl3).

Workup

  1. waitleft
  2. waitto stand overnight
  3. customthe methanol is evaporated under reduced pressure
  4. dissolutionThe crude product is dissolved in 25 ml of water
  5. washwashed twice with 20 ml of diethyl ether
  6. extractionsaturated with sodium chloride and extracted with 3×25 ml of dichloromethane
  7. dry with materialThe organic phase is dried over magnesium sulphate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. distillationthe crude product distilled

Sources & evidence

ORD record
ord-88ebe0a4089a43fc83a6dd6a91de9f79
Source dataset
uspto-grants-1993_09
Patent number
US05243062

Reaction notes

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