Methoxymethyl-triphenylphosphonium chloride → HCID 123164601, compound

HRID 2178523Notes

Reaction equation

HRID 2178523 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[O:30]=[C:31]1[CH2:36][CH2:35][CH2:34][CH2:33][N:32]1[C:37]1[C:42]([CH:43]=O)=[CH:41][CH:40]=[CH:39][N:38]=1>O1CCCC1.CO>[CH3:2][O:3][CH:4]=[CH:43][C:42]1[C:37]([N:32]2[CH2:33][CH2:34][CH2:35][CH2:36][C:31]2=[O:30])=[N:38][CH:39]=[CH:40][CH:41]=1

Participants

6

Reactant 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxideHCID 89500826HCID 89500826, compound

Product 1

HCID 123164601HCID 123164601, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Methoxymethyl-triphenylphosphonium chloride (3.59 g, 10.48 mmol, 1.3 eq) is dissolved in dry tetrahydrofuran (150 ml) under nitrogen. This solution is cooled at 0° C. and potassium tert-butoxide (1.085 g, 9.67 mmol, 1.2 eq) is added. The reaction mixture is stirred at 0° C. for 30 min. A solution of crude 2-(2-oxopiperidin-1-yl)pyridine-3-carbaldehyde a4-1 (4.2 g, 8.06 mmol, 1 eq) in dry THF (50 ml) is added, then the reaction mixture is warmed up to room temperature and stirred for 1 hour. The solvent is removed under reduced pressure, the residue is taken with ethyl acetate, stirred, filtered and the solid cake washed with ethyl acetate (2 times). The filtrate is evaporated under reduced pressure. The residue is purified by chromatography over silicagel (gradient: CH2Cl2/MeOH/NH4OH 100/0/0 to 97/3/0.3). The product obtained is redissolved in methanol, catched over an acidic column, washed with methanol and then released with ammonia 1M in methanol. The solvent is evaporated under reduced pressure to afford 540 mg of 1-[3-(2-methoxyethenyl)pyridin-2-yl]piperidin-2-one a4-2.

Workup

  1. temperaturethe reaction mixture is warmed up to room temperature
  2. stirringstirred for 1 hour
  3. customThe solvent is removed under reduced pressure
  4. stirringstirred
  5. filtrationfiltered
  6. washthe solid cake washed with ethyl acetate (2 times)
  7. customThe filtrate is evaporated under reduced pressure
  8. customThe residue is purified by chromatography over silicagel (gradient: CH2Cl2/MeOH/NH4OH 100/0/0 to 97/3/0.3)
  9. customThe product obtained
  10. washwashed with methanol
  11. customThe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-7e17041297da4864a963aae3292f5a13
Source dataset
uspto-grants-2015_06
Patent number
US09067930B2

Reaction notes

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