Triethylamine → HCID 22851231, compound

HRID 1463783Notes

Reaction equation

HRID 1463783 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([O:13][CH2:14][P:15]([O:21][CH:22]([CH3:24])[CH3:23])([O:17][CH:18]([CH3:20])[CH3:19])=[O:16])[CH2:11]I)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[H][H]>CO.[Pd]>[CH2:1]([O:8][CH2:9][C@@H:10]([O:13][CH2:14][P:15]([O:21][CH:22]([CH3:24])[CH3:23])([O:17][CH:18]([CH3:19])[CH3:20])=[O:16])[CH3:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 22851228(R)-1-(benzyloxy)-2-[(diisopropylphosphono)methoxy]-3-iodopropaneHCID 178418361HCID 178418361, compound

Product 1

HCID 22851231HCID 22851231, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (R)-1-(benzyloxy)-2-[(diisopropylphosphono)methoxy]-3-iodopropane (12.0 g, 25.5 mmol) in 15 mL of methanol was treated with triethylamine (3.10 g, 30.6 mmol) and 10% palladium on carbon (2.0 g), and the mixture was placed under 40 psi hydrogen atmosphere in a Parr shaker apparatus. After 2 hours, the reaction mixture was filtered through a 1" pad of Celite, and the collected solid was washed with methanol. The filtrate was concentrated and treated with ethyl acetate (200 mL). The precipitate was removed by filtration, the filtrate was concentrated in vacuo, and the residue was purified by column chromatography on silica gel (10:1, 75% ethyl acetate/hexane) to afford 8.24 g (94%) of the title compound as a clear, colorless oil.

Workup

  1. filtrationthe reaction mixture was filtered through a 1" pad of Celite
  2. washthe collected solid was washed with methanol
  3. concentrationThe filtrate was concentrated
  4. additiontreated with ethyl acetate (200 mL)
  5. customThe precipitate was removed by filtration
  6. concentrationthe filtrate was concentrated in vacuo
  7. customthe residue was purified by column chromatography on silica gel (10:1, 75% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-45a3accc2d784cc7be525a08959560a6
Source dataset
uspto-grants-1994_04
Patent number
US05302585

Reaction notes

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