1,3-Dibromopropane → Tert-butyl 1-cyanocyclobutane-1-carboxylate

HRID 1480980Notes

Reaction equation

HRID 1480980 reaction equation
[CH2:1]1[CH2:11]C[N:9]2[C:4](=NCCC2)[CH2:3][CH2:2]1.[C:12]([O:16][C:17](=[O:21])CC#N)([CH3:15])([CH3:14])[CH3:13].BrCCCBr>CN(C=O)C.CCOC(C)=O>[C:12]([O:16][C:17]([C:3]1([C:4]#[N:9])[CH2:2][CH2:1][CH2:11]1)=[O:21])([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 70693tert-Butyl cyanoacetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 66797886Tert-butyl 1-cyanocyclobutane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

DBU (23.5 mL) was added slowly to a solution of cyano-acetic acid tert-butyl ester (8.84 g) in DMF (100 mL) at rt, followed by addition of 1,3-dibromopropane (13.9 g); then the reaction mixture was stirred in an oil bath (bath temperature=80° C.) overnight. The reaction was cooled, diluted with EtOAc, then washed with cold water, dil. NaCl solution; EtOAc phase was dried over anhydrous sodium sulfate, filtered, concentrated, the residue was column purified to give title compound (6.58 g). 1H NMR in CDCl3, δ in ppm: 2.8-2.5 (m, 4H), 2.4-2.2 (m, 2H), 1.51 (s, 9H).

Workup

  1. temperatureThe reaction was cooled
  2. washwashed with cold water, dil. NaCl solution
  3. dry with materialEtOAc phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified

Sources & evidence

ORD record
ord-0067a61662a244fe9fe2ef3f1ed557a8
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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