Ammonia → HCID 19090882, compound

HRID 1612718Notes

Reaction equation

HRID 1612718 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:18][N+:19]([O-])=O)[CH2:9][P:10]([CH3:17])(=[O:16])[O:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:4][CH:3]=1.N.[H][H]>C(O)C.[Ni]>[NH2:19][CH2:18][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH2:9][P:10]([CH3:17])(=[O:16])[O:11][CH2:12][CH:13]([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 19090918Isobutyl 2-(4-fluorophenyl)-3-nitro-propyl(methyl)phosphinateHCID 178418361HCID 178418361, compound

Product 1

HCID 19090882HCID 19090882, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 11.6 g of isobutyl 2-(4-fluorophenyl)-3-nitro-propyl(methyl)phosphinate in 100 ml of ethanol is added to 114 g of a 8% solution of ammonia in ethanol. To this are added 9 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 to give isobutyl 3-amino-2-(4-fluorophenyl)-propyl-(methyl)phosphinate as a viscous oil, 31P N.M.R. spectrum: δ=+54.0 and +53.4 ppm (CDCl3).

Workup

  1. filtrationThe mixture is then filtered
  2. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-2d998e54a6ad41e68535dd0fc0df4a13
Source dataset
uspto-grants-1993_03
Patent number
US05190933

Reaction notes

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