Water → Tert-butyl 4-(1-cyano-2-oxoethyl)piperidine-1-carboxylate

HRID 1616076Notes

Reaction equation

HRID 1616076 reaction equation
[C:1]([CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)#[N:2].C[C:18](C)([O-:20])C.[K+].C(OCC)=O.O>CN(C)C=O>[C:1]([CH:3]([CH:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9]1)[CH:18]=[O:20])#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8025Ethyl formateHCID 22248390tert-Butyl 4-(cyanomethyl)piperidine-1-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 86681870Tert-butyl 4-(1-cyano-2-oxoethyl)piperidine-1-carboxylateYield 93.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under an argon atmosphere, tert-butyl 4-(cyanomethyl)piperidine-1-carboxylate (2.24 g, 10 mmol) and potassium tert-butoxide (6.73 g, 60 mmol) were dissolved in anhydrous N,N-dimethyl formamide (15 mL), and a solution of ethyl formate (4.44 g, 60 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added dropwise under ice-cooling. The temperature was gradually raised to room temperature, and then the resultant mixture was stirred overnight. Water was added to the reaction liquid, followed by extraction with ethyl acetate. 1 N hydrochloric acid was added to the obtained aqueous layer until it reached a pH of 6, and then the resultant mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under a reduced pressure to give tert-butyl 4-(1-cyano-2-oxoethyl)piperidine-1-carboxylate (2.35 g) as a crude product.

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. addition1 N hydrochloric acid was added to the obtained aqueous layer until it
  4. extractionthe resultant mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-d364429de8bf43caa335d4507d73cf59
Source dataset
uspto-grants-2014_07
Patent number
US08765771B2

Reaction notes

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