1,2-Dimethoxyethane → Tert-butyl 4-cyanopiperidine-1-carboxylate

HRID 1748512Notes

Reaction equation

HRID 1748512 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S([CH2:24][N:25]=C=O)(=O)=O)=CC=1.COCCOC.CC(C)([O-])C.[K+]>O.C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:24]#[N:25])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 117890781-Isocyanatomethanesulfonyl-4-methylbenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 1514443Tert-butyl 4-cyanopiperidine-1-carboxylateYield 58.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-tert-Butyloxycarbonyl-4-piperidone (13 g) and p-toluenesulfonylmethylisocyanate (16.6 g) were added to 1,2-dimethoxyethane (90 ml) and ethanol (10 ml). The solution was cooled in ice, potassium tert-butoxide (8.3 g) was added thereto under stirring and the mixture was stirred at room temperature for 6.5 hours. Water was added to the reaction solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo and the resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 4-cyanopiperidine-1-carboxylic acid tert-butyl ester (8.0 g) as a solid.

Workup

  1. temperatureThe solution was cooled in ice
  2. stirringthe mixture was stirred at room temperature for 6.5 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customthe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b13ea7abe0504134a956e8af7ae45b31
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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