Ammonia → isobutyl P-(4-aminobut-2-yl)-P-methyl-phosphinate

HRID 865838Notes

Reaction equation

HRID 865838 reaction equation
[C:1]([CH2:3][CH:4]([P:6]([CH3:13])(=[O:12])[O:7][CH2:8][CH:9]([CH3:11])[CH3:10])[CH3:5])#[N:2].N.[H][H]>C(O)C.[Ni]>[NH2:2][CH2:1][CH2:3][CH:4]([P:6]([CH3:13])(=[O:12])[O:7][CH2:8][CH:9]([CH3:10])[CH3:11])[CH3:5]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 23374761isobutyl P-(3-cyanoprop-2-yl)-P-methyl-phosphinateHCID 178418361HCID 178418361, compound

Product 1

HCID 23374771isobutyl P-(4-aminobut-2-yl)-P-methyl-phosphinate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 29.8 g of isobutyl P-(3-cyanoprop-2-yl)-P-methyl-phosphinate in 200 ml of ethanol is added to 310.0 g of an 8% solution of ammonia in ethanol. To this are added 20 ml of Raney nickel slurry, and the resulting mixture is hydrogenated at 1 bar until hydrogen uptake ceases. The mixture is then filtered and the filtrate is concentrated under reduced pressure. The crude product is distilled under reduced pressure to give isobutyl P-(4-aminobut-2-yl)-P-methyl-phosphinate, b.p. 100°/0.1 mbar, 31P-NMR spectrum: δ=+58.9 and +58.4 ppm (CDCl3).

Workup

  1. filtrationThe mixture is then filtered
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. distillationThe crude product is distilled under reduced pressure

Sources & evidence

ORD record
ord-ff0d557d4fb147cfad3a2b52fcc4d40c
Source dataset
uspto-grants-1996_10
Patent number
US05567840

Reaction notes

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