Sodium Hydroxide → tert-Butyl 4-oxopiperidine-1-carboxylate

HRID 1634856Notes

Reaction equation

HRID 1634856 reaction equation
Cl.O.[NH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.[OH-].[Na+].[C:12]([O:16][C:17](=O)[O:18]C(C)(C)C)([CH3:15])([CH3:14])[CH3:13]>O>[C:12]([O:16][C:17]([N:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2723901PiperonylamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Water (250 ml) was added to 4-piperidone monohydrate hydrochloride salt (75 g) for dissolution, and 1 N aqueous solution of sodium hydroxide (1000 ml) was added thereto. To the solution, ditertiarybutylcarbonate (120 g) was added dropwise with stirring under cooling on ice, and the mixture was vigorously stirred for 6 hours at room temperature. The reaction mixture was subjected to extraction with ethyl acetate, and the extract was evaporated to dryness under reduced pressure to thereby yield a pale yellow solid. By recrystallization of the solid from hexane, N-t-butyloxycarbonyl-4-piperidone (3) (38.9 g) was obtained in the form of white needle-shaped crystals.

Workup

  1. additionwas added
  2. temperatureunder cooling on ice
  3. stirringthe mixture was vigorously stirred for 6 hours at room temperature
  4. extractionThe reaction mixture was subjected to extraction with ethyl acetate
  5. customthe extract was evaporated to dryness under reduced pressure
  6. customto thereby yield a pale yellow solid
  7. customBy recrystallization of the solid from hexane

Sources & evidence

ORD record
ord-45e8d63060c5449f873c438099cc758f
Source dataset
uspto-grants-2003_01
Patent number
US06509003B2

Reaction notes

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