Hydrochloric Acid → Tert-butyl 4-(2-methoxy-2-oxoethylidene)piperidine-1-carboxylate

HRID 217960Notes

Reaction equation

HRID 217960 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]([CH2:7]P(OC)(OC)=O)=[O:6].O=[C:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1.Cl>C(O)C>[CH3:3][O:4][C:5]([CH:7]=[C:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 80029Trimethyl phosphonoacetateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 10377658Tert-butyl 4-(2-methoxy-2-oxoethylidene)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium hydroxide (4.56 g, 0.114 mol) was dissolved in ethanol (210 mL), and trimethyl phosphonoacetate (11.4 g, 0.062 mol) added with stirring. The mixture was stirred for 30 min at room temperature. Tert-butyl 4-oxopiperidine-1-carboxylate (11.35 g, 0.057 mol) was added with stirring at room temperature, and the reaction was allowed to stand overnight. Then, the mixture was acidified with diluted hydrochloric acid until the pH was 4, filtered, concentrated, and partitioned into water and chloroform. Phases were separated. The aqueous phase was extracted once with chloroform. Chloroform phases were combined, washed once with brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was evaporated in vacuo to give the title compound.

Workup

  1. stirringThe mixture was stirred for 30 min at room temperature
  2. stirringwith stirring at room temperature
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompartitioned into water and chloroform
  6. customPhases were separated
  7. extractionThe aqueous phase was extracted once with chloroform
  8. washwashed once with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-0377f12aa6b04ce4951befdc77827765
Source dataset
uspto-grants-2012_06
Patent number
US08198301B2

Reaction notes

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