HCID 10702957, compound → HCID 10584033, compound

HRID 2289201Notes

Reaction equation

HRID 2289201 reaction equation
[OH:1][C@@H:2]([P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9])[CH:3]=[C:4]([CH3:6])[CH3:5]>CO.[Pd]>[OH:1][C@@H:2]([P:7](=[O:12])([O:8][CH3:9])[O:10][CH3:11])[CH2:3][CH:4]([CH3:5])[CH3:6]

Participants

4

Procedure

Dimethyl (S)-1-hydroxy-3-methyl-2-butenylphosphonate obtained in Example 31 (68% e.e., 54 mg) was dissolved in 10 ml of methanol, and 10% Pd/C (16 mg) was added thereto. The mixture was stirred at room temperature for 3 hours under hydrogen atmosphere. The reaction mixture was filtered through Celite and the filter cake was washed with ethyl acetate. The solvent was distilled under reduced pressure and the residue was purified by flash column chromatography (acetone/hexane=1/4, on SiO2) to obtain dimethyl (S)-1-hydroxy-3-methylbutylphosphonate as a final product in a yield of 98%. This compound is known to be useful as a raw material for medicines and the like. The chemical reaction in this Reference Example is shown in chemical formula 49. ##STR43##

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washthe filter cake was washed with ethyl acetate
  3. distillationThe solvent was distilled under reduced pressure
  4. customthe residue was purified by flash column chromatography (acetone/hexane=1/4, on SiO2)

Sources & evidence

ORD record
ord-69c090428c1b4d8faac82b81ac517141
Source dataset
uspto-grants-2000_07
Patent number
US06090969

Reaction notes

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