1,1-Dimethylethyl 4-[(1E)-4-(dimethoxyphosphinyl)-3-oxo-1-buten-1-yl]-1-piperidinecarboxylate → HCID 21993678, compound

HRID 1978367Notes

Reaction equation

HRID 1978367 reaction equation
[CH3:1][O:2][P:3]([CH2:7][C:8](=[O:24])/[CH:9]=[CH:10]/[CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)([O:5][CH3:6])=[O:4]>CO.[Pd]>[CH3:1][O:2][P:3]([CH2:7][C:8](=[O:24])[CH2:9][CH2:10][CH:11]1[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:15][CH2:16]1)([O:5][CH3:6])=[O:4]

Participants

4

Reactant 1

HCID 1317225781,1-Dimethylethyl 4-[(1E)-4-(dimethoxyphosphinyl)-3-oxo-1-buten-1-yl]-1-piperidinecarboxylate

Product 1

HCID 21993678HCID 21993678, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 5.443 g (15.062 mM) of tert-butyl (E)-4-[4-(dimethoxyphosphoryl)-3-oxo-1-butenyl]piperidine-1-carboxylate in 50 ml of methanol was subjected to hydrogenation using 3 g of 10% palladium-on-carbon (50% hydrous) as a catalyst at room temperature and atmospheric pressure until the starting material had been no longer detected. The catalyst was removed by filtration with the aid of celite and the catalyst was washed with methanol. The filtrate and washes were pooled and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate:1/1 to ethyl acetate) to provide the title compound.

Workup

  1. customat room temperature
  2. customThe catalyst was removed by filtration with the aid of celite
  3. washthe catalyst was washed with methanol
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate:1/1 to ethyl acetate)

Sources & evidence

ORD record
ord-68d15202cf8b4550b80bd92b7b03beb8
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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