Ethyl 3-amino-2-phenylpropyl(diethoxymethyl)phosphinate → Ethyl 3-amino-2-cyclohexylpropyl(diethoxymethyl)phosphinate

HRID 2209942Notes

Reaction equation

HRID 2209942 reaction equation
[NH2:1][CH2:2][CH:3]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[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)(C)(C)C.[Rh]>[NH2:1][CH2:2][CH:3]([CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1)[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

4

Reactant 1

HCID 14362832Ethyl 3-amino-2-phenylpropyl(diethoxymethyl)phosphinate

Product 1

HCID 19379613Ethyl 3-amino-2-cyclohexylpropyl(diethoxymethyl)phosphinate

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 6386tert-ButanolSolvent2×

Procedure

A solution of 3.45 g of ethyl 3-amino-2-phenylpropyl(diethoxymethyl)phosphinate in 25 ml of tertiary butanol is added to 2.0 g of 5% rhodium in alumina, suspended in 25 ml of tertiary butanol. The resulting mixture is hydrogenated at an atmosphere of 150 bar and temperature of 100° C. for a period of 20 hours. The mixture is then filtered and the filtrate is concentrated under reduced pressure. The crude product is chromatographed on silica gel using ethanol as eluent to give ethyl 3-amino-2-cyclohexylpropyl(diethoxymethyl)phosphinate as a viscous oil, 31 p=47.1 and +47.0 ppm (CDCl3).

Workup

  1. filtrationThe mixture is then filtered
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe crude product is chromatographed on silica gel

Sources & evidence

ORD record
ord-2da5a06975b6462a96f7ea7fe797fa35
Source dataset
uspto-grants-1995_10
Patent number
US05457095

Reaction notes

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