Water → Butyl ethyl(2-methyl-3-aminopropyl)phosphinate

HRID 576016Notes

Reaction equation

HRID 576016 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([P:9]([CH2:16][CH:17]([C:19]#[N:20])[CH3:18])(=[O:15])[O:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH3:8].O>C(OCC)C>[CH2:7]([P:9]([CH2:16][CH:17]([CH3:18])[CH2:19][NH2:20])(=[O:15])[O:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 86657307Butyl ethyl(2-cyano-2-methylethyl)phosphinate

Product 1

HCID 46212766Butyl ethyl(2-methyl-3-aminopropyl)phosphinateYield 85%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

At room temperature, 2.3 g (0.06 mol) of lithium aluminum hydride in 100 ml absolute diethyl ether in a three-neck flask equipped with stirrer, dropping funnel and high-performance condenser are, while continuously stirring, admixed with a solution of 21.7 g (0.1 mol) of butyl ethyl(2-cyano-2-methylethyl)phosphinate (produced similarly to Example 10) in 100 ml of diethyl ether added dropwise at such a rate that there is a moderate boil of the diethyl ether. This is followed by refluxing for 1 hour and admixing of the reaction solution with 1.8 g (0.1 mol) of water, and the insoluble salts are filtered off, the solvent is removed in vacuo and the product is purified by chromatography to obtain 18.8 g (85% of theory) of butyl ethyl(2-methyl-3-aminopropyl)phosphinate as colorless oil.

Workup

  1. additionadded dropwise at such a rate that there
  2. temperatureby refluxing for 1 hour
  3. customthe solvent is removed in vacuo
  4. customthe product is purified by chromatography

Sources & evidence

ORD record
ord-7e10142155f94469bce8953c91e76543
Source dataset
uspto-grants-2015_05
Patent number
US09035088B2

Reaction notes

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