Triethylamine → HCID 15667220, compound

HRID 1463781Notes

Reaction equation

HRID 1463781 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 15667219(S)-1-(Benzyloxy)-2-[(diisopropylphosphono)methoxy]-3-iodopropaneHCID 178418361HCID 178418361, compound

Product 1

HCID 15667220HCID 15667220, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-1-(Benzyloxy)-2-[(diisopropylphosphono)methoxy]-3-iodopropane (11.1 g, 23.5 mmol) was mixed with triethylamine (2.85 g, 28.2 mmol) in 15 mL of methanol. To this solution, 10% palladium on carbon (2.0 g) was added under nitrogen atmosphere. The reaction was performed in a Parr apparatus at a hydrogen pressure of 40 psi. After 3 hours, the catalyst was removed by filtration, the filtrate was concentrated, and the residue was purified by flash chromatography on silica gel (methylene chloride:acetone=1:0 to 5:1) to give 7.91 g (98%) of the title compound as an oil.

Workup

  1. customthe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by flash chromatography on silica gel (methylene chloride:acetone=1:0 to 5:1)

Sources & evidence

ORD record
ord-548c6323f674424081f7906025a26c22
Source dataset
uspto-grants-1994_04
Patent number
US05302585

Reaction notes

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