Water → Diethyl 2-(3,4-dimethyl-5-phenyloxazolidin-2-yl)benzylphosphonate

HRID 1197749Notes

Reaction equation

HRID 1197749 reaction equation
[CH:1]([C:3]1[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=1[CH2:5][P:6](=[O:13])([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9])=[O:2].[CH3:18][C@H:19]([NH:28][CH3:29])[C@H:20](O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>C1C=CC=CC=1>[CH3:29][N:28]1[CH:19]([CH3:18])[CH:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:2][CH:1]1[C:3]1[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=1[CH2:5][P:6](=[O:13])([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 962WaterHCID 9294EphedrineHCID 19104780Diethyl 2-formylbenzylphosphonate

Product 1

HCID 19104778Diethyl 2-(3,4-dimethyl-5-phenyloxazolidin-2-yl)benzylphosphonate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2.0 g (8 mmol) of the compound A and 1.32 g (8 mmol) of (-)-ephedrine were dissolved in 100 ml of benzene and heated under reflux in a water separator for 24 h. The solvent was then removed by rotary evaporation and the residue was chromatographed on silica gel (eluent CH2Cl2 /ethanol 9.5/0.5; Rf=0.55). The product F was obtained as an oil.

Workup

  1. temperatureheated
  2. customThe solvent was then removed by rotary evaporation
  3. customthe residue was chromatographed on silica gel (eluent CH2Cl2 /ethanol 9.5/0.5; Rf=0.55)

Sources & evidence

ORD record
ord-698f46525b45450794793f3ed944a5db
Source dataset
uspto-grants-1994_01
Patent number
US05278152

Reaction notes

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