Ethyl Acetate → Tert-butyl 4-(4-cyanophenyl)-2-oxopiperidine-1-carboxylate

HRID 541415Notes

Reaction equation

HRID 541415 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].C(OCC)(=[O:24])C>O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:13](=[O:24])[CH2:14]2)=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 22492960Tert-butyl 4-(4-cyanophenyl)piperidine-1-carboxylate2×

Product 1

HCID 68352653Tert-butyl 4-(4-cyanophenyl)-2-oxopiperidine-1-carboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a round-bottom flask, was placed a solution of tert-butyl 4-(4-cyanophenyl)piperidine-1-carboxylate (compound 1.4, 515 mg, 1.80 mmol, 1.00 equiv) in ethyl acetate (5 mL). A solution of NaIO4 (963 mg, 4.50 mmol, 2.50 equiv) in water (5 mL) and RuCl3 (74.7 mg, 0.36 mmol, 0.20 equiv) was carefully added. The resulting mixture was stirred overnight at room temperature. The solids were removed by filtration and the filtrate was washed with 2×20 mL of water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to yield 432 mg (80%) of the title compound as a light yellow oil.

Workup

  1. customInto a round-bottom flask, was placed
  2. customThe solids were removed by filtration
  3. washthe filtrate was washed with 2×20 mL of water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7972df5baf824fe190460f9bef425ecc
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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