Isopropyltriphenylphosphonium iodide → HCID 18677004, compound

HRID 1634032Notes

Reaction equation

HRID 1634032 reaction equation
[I-].[CH:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([CH3:4])[CH3:3].C([Li])CCC.[CH:29]([CH:31]([NH:40][C:41]([CH:43]([NH:48][C:49](=[O:58])[O:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[CH2:44][CH:45]([CH3:47])[CH3:46])=[O:42])[CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=O>C1COCC1.O.C(OCC)(=O)C>[CH3:46][CH:45]([CH3:47])[CH2:44][CH:43]([NH:48][C:49](=[O:58])[O:50][CH2:51][C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1)[C:41](=[O:42])[NH:40][CH:31]([CH2:32][CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[CH:29]=[C:2]([CH3:4])[CH3:3]

Participants

7

Reactant 3

HCID 2723783Isopropyltriphenylphosphonium iodideHCID 10158494HCID 10158494, compoundHCID 178418339Butyllithium

Product 1

HCID 18677004HCID 18677004, compoundYield 16.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

A solution comprised of isopropyltriphenylphosphonium iodide (13.02 g, 30.1 mmol) in TBF (80 mL) was cooled to −78° C. and then n-butyllithium (12.44 mL, 2.5M in hexane) was added. The mixture was stirred for 5 minutes, heated to room temperature and stirred for an additional 25 minutes. Benzyl 1-(1-formyl-3-phenylpropylcarbamoyl)-3-methylbutylcarbamate (4.12 g, 10.04 mmol), prepared as in the procedure set forth in Synthesis, 1983, pp 676-678, was dissolved in THF (40mL) and the solution was added dropwise. The mixture was stirred for 18 hours at room temperature and then diluted with water (5 mL) and ethyl acetate (250 mL). The organic layer was washed with 1M hydrochloric acid, saturated aqueous sodium bicarbonate and brine, dried (MgSO4) and concentrated to dryness in vacuo. Product was purified from the residue by column chromatography using 20% ethyl acetate/hexane to provide benzyl 3-methyl-1-(3-methyl-1-phenethylbut-2-enylcarbamoyl)butylcarbamate (0.75 g, 1.68 mmol) as a clear oil.

Workup

  1. temperatureheated to room temperature
  2. stirringstirred for an additional 25 minutes
  3. customset forth in Synthesis, 1983, pp 676-678
  4. additionthe solution was added dropwise
  5. stirringThe mixture was stirred for 18 hours at room temperature
  6. washThe organic layer was washed with 1M hydrochloric acid, saturated aqueous sodium bicarbonate and brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated to dryness in vacuo
  9. customProduct was purified from the residue by column chromatography

Sources & evidence

ORD record
ord-943af5615c6b4232bcc67b6c7d65dded
Source dataset
uspto-grants-2003_01
Patent number
US06506733B1

Reaction notes

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