Acetic Acid → 3-(p-Chlorobenzylamino)propyl(tetrahydrofuran-2-yl)phosphinic acid ethyl ester

HRID 1654471Notes

Reaction equation

HRID 1654471 reaction equation
[CH2:1]([O:3][P:4]([CH2:13][CH2:14][CH2:15][NH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)([CH:6](OCC)[O:7][CH2:8][CH3:9])=[O:5])[CH3:2].C=O.[C:27](O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH2:1]([O:3][P:4]([CH2:13][CH2:14][CH2:15][NH:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)([CH:6]1[CH2:27][CH2:9][CH2:8][O:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 544329463-(p-Chlorobenzylamino)propyl(diethoxymethyl)phosphinic acid ethyl ester

Product 1

HCID 544480033-(p-Chlorobenzylamino)propyl(tetrahydrofuran-2-yl)phosphinic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.5 g of 3-(p-chlorobenzylamino)propyl(diethoxymethyl)phosphinic acid ethyl ester are dissolved in 10 ml of methanol, 0.36 g (0.53 ml)of a 35% aqueous formaldehyde solution is added, and the mixture is stirred at room temperature for one hour. 0.4 g of glacial acetic acid and 0.40 g of sodium cyanoborohydride are added, and the mixture is stirred at room temperature for 2 hours, concentrated by evaporation under reduced pressure, taken up in dichloromethane and washed with 5% aqueous sodium hydrogen carbonate solution. The organic phase is separated off, dried over sodium sulfate and concentrated by evaporation under reduced pressure. The oily residue is purified by chromatography on silica gel, yielding 3-(p-chlorobenzylamino)propyl(tetrahydrofuran-2-yl)phosphinic acid ethyl ester in the form of a colourless oil.

Workup

  1. stirringthe mixture is stirred at room temperature for 2 hours
  2. concentrationconcentrated by evaporation under reduced pressure
  3. washwashed with 5% aqueous sodium hydrogen carbonate solution
  4. customThe organic phase is separated off
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe oily residue is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-7e911492944240db9b31d58e1d151f59
Source dataset
uspto-grants-1995_04
Patent number
US05407922

Reaction notes

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