Cyanuric chloride → Tert-butyl 6-cyano-3-azabicyclo[3.1.0]hexane-3-carboxylate

HRID 455286Notes

Reaction equation

HRID 455286 reaction equation
[C:1]([CH:4]1[CH:9]2[CH:5]1[CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8]2)(=O)[NH2:2].N1C(Cl)=NC(Cl)=NC=1Cl>CN(C=O)C.O>[C:1]([CH:4]1[CH:5]2[CH:9]1[CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6]2)#[N:2]

Participants

5

Reactant 2

HCID 7954Cyanuric chlorideHCID 70222027tert-Butyl 6-carbamoyl-3-azabicyclo[3.1.0]hexane-3-carboxylate

Product 1

HCID 59529950Tert-butyl 6-cyano-3-azabicyclo[3.1.0]hexane-3-carboxylateYield 99.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2 (1.83 g, 8.09 mmol) in DMF (30 mL) was added cyanuric chloride (1.50 g, 8.09 mmol) and stirred for 2 h. The reaction was diluted with water (100 mL) and extracted with EtOAc (2×80 mL). The combined organic extracts were washed with water (2×100 mL), brine (120 mL), dried over MgSO4 and concentrated under vacuum to afford 3 (1.67 g, 99%) as a clear yellow oil; 1H-nmr (400 MHz, CDCl3) δ 3.80-3.58 (m, 2H), 3.40 (d, J=12.0 Hz, 2H), 2.16 (s, 2H), 1.43 (s, 9H), 1.25 (t, J=3.0 Hz, 1H).

Workup

  1. extractionextracted with EtOAc (2×80 mL)
  2. washThe combined organic extracts were washed with water (2×100 mL), brine (120 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e3db20425e5e4d238aff024f181d1f06
Source dataset
uspto-grants-2013_07
Patent number
US08497289B2

Reaction notes

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