Acetic Acid → HCID 54448003, compound

HRID 484003Notes

Reaction equation

HRID 484003 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 54448003HCID 54448003, compound

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-3f7a913ee54140a2ad8a5952b199b863
Source dataset
uspto-grants-1993_07
Patent number
US05229379

Reaction notes

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