Pyridine → 1-tert-Butyl 3-ethyl 3-cyanoazetidine-1,3-dicarboxylate

HRID 1175152Notes

Reaction equation

HRID 1175152 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:17](=O)[NH2:18])[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]1)=[O:5])[CH3:2].N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1([C:17]#[N:18])[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 595583791-(1,1-Dimethylethyl) 3-ethyl 3-(aminocarbonyl)-1,3-azetidinedicarboxylate

Product 1

HCID 595585001-tert-Butyl 3-ethyl 3-cyanoazetidine-1,3-dicarboxylateYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Carbamoyl-azetidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (25.4 g; 93.5 mmol) is dissolved in THF (260 ml) and pyridine (19.2 g; 243 mmol) and cooled to 0° C. under stirring. Trifluoroacetic acid anhydride (26.4 ml; 187 mmol) is added dropwise over 10 minutes, the mixture warmed to room temperature and stirred for 30 minutes, poured on water and extracted with TBME three times. The combined organic phases are dried over Na2SO4, filtered, evaporated and purified via chromatography (SiO2; heptane/TBME 6:4) to yield the title compound as light brown oil (22.4 g; 94%).

Workup

  1. stirringstirred for 30 minutes
  2. additionpoured on water
  3. extractionextracted with TBME three times
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. custompurified via chromatography (SiO2; heptane/TBME 6:4)

Sources & evidence

ORD record
ord-ea76da750e454940960ed21e618ce667
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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