Ammonia → Ethyl 3-amino-2-benzylpropyl(diethoxymethyl)phosphinate

HRID 5186Notes

Reaction equation

HRID 5186 reaction equation
[CH2:1]([CH:8]([C:22]#[N:23])[CH2:9][P:10]([CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])(=[O:14])[O:11][CH2:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N.[H][H]>C(O)C.[Ni]>[NH2:23][CH2:22][CH:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:9][P:10]([CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])(=[O:14])[O:11][CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 14362814Ethyl 2-benzyl-2-cyanoethyl(diethoxymethyl)phosphinateHCID 178418361HCID 178418361, compound

Product 1

HCID 14362816Ethyl 3-amino-2-benzylpropyl(diethoxymethyl)phosphinate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 3.5 g of ethyl 2-benzyl-2-cyanoethyl(diethoxymethyl)phosphinate in 50 ml of ethanol is added to 25 g of an 8% solution of ammonia in ethanol. To this are added 2 ml of Raney Nickel and the resulting mixture is hydrogenated at 1 bar until the theoretical amount of hydrogen has been taken up. The mixture is then filtered and the filtrate is concentrated under reduced pressure to give ethyl 3-amino-2-benzylpropyl(diethoxymethyl)phosphinate as a viscous oil, 31P=+46.3 ppm (CDCl3).

Workup

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

Sources & evidence

ORD record
ord-37b50643042144889ddbf8ea19fd8458
Source dataset
uspto-grants-1993_09
Patent number
US05243062

Reaction notes

Loading…