Ethanol → Ethyl (2-aminoethyl)(methyl)phosphinate

HRID 1614912Notes

Reaction equation

HRID 1614912 reaction equation
[CH2:1]([O:3][P:4]([CH2:7][CH2:8][NH:9]C(OCC1C=CC=CC=1)=O)([CH3:6])=[O:5])[CH3:2].CCO>[Pd].CCOC(C)=O>[CH2:1]([O:3][P:4]([CH2:7][CH2:8][NH2:9])([CH3:6])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 702EthanolHCID 67033999(2-Benzyloxycarbonylamino-ethyl)-methyl-phosphinic acid ethyl ester

Product 1

HCID 85676205Ethyl (2-aminoethyl)(methyl)phosphinateYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(2-Benzyloxycarbonylamino-ethyl)-methyl-phosphinic acid ethyl ester (1.3 g, 4.56 mmol) and 10% Pd/C (485 mg) were combined in a flask and EtOH (46 mL) was added. The reaction flask atmosphere was exchanged for H2 and the reaction was run at room temperature until complete, as determined by TLC (eluent: 100% EtOAc). The reaction was then filtered through Supercell NF and the filtrate was concentrated to yield (2-amino-ethyl)-methyl-phosphinic acid ethyl ester (615 mg, 90%) as a yellow oil in which white crystals began to form under high vacuum.

Workup

  1. customwas run at room temperature
  2. filtrationThe reaction was then filtered through Supercell NF
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-8cd9e3c53e524f6ca27a6afb6d161606
Source dataset
uspto-grants-2014_07
Patent number
US08765722B2

Reaction notes

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