Cyanuric chloride → (1-Cyano-spiro[2.5]oct-1-ylmethyl)-carbamic acid tert-butyl ester

HRID 1297227Notes

Reaction equation

HRID 1297227 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][C:9]1([C:17](=O)[NH2:18])[C:11]2([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].N1C(Cl)=NC(Cl)=NC=1Cl.[OH-].[Na+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][C:9]1([C:17]#[N:18])[C:11]2([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7954Cyanuric chlorideHCID 14798Sodium HydroxideHCID 69515965(1-Carbamoyl-spiro[2.5]oct-1-ylmethyl)-carbamic acid tert-butyl ester

Product 1

HCID 69515964(1-Cyano-spiro[2.5]oct-1-ylmethyl)-carbamic acid tert-butyl esterYield 98.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(1-carbamoyl-spiro[2.5]oct-1-ylmethyl)-carbamic acid tert-butyl ester (13.1 g, 46.4 mmol) was suspended in DMF (400 mL) and cooled in an ice bath. Cyanuric chloride (11.8 g, 64.9 mmol) was added. After 20 minutes the solution was homogeneous and after 30 minutes a new precipitate began to form. After 1 hour, the mixture was poured over 0.5N NaOH (500 mL) with ice bath cooling and then transferred to a separatory funnel. The solution was extracted with ethyl acetate (3×400 mL). The combined organic layers were washed with brine (2×400 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was dissolved in ethyl acetate (300 mL), washed with brine (3×300 mL), dried over sodium sulfate, filtered and evaporated to give 12.1 g (98%) of (1-cyano-spiro[2.5]oct-1-ylmethyl)-carbamic acid tert-butyl ester as an off-white solid: 1H NMR (300 MHz, CDCl3) δ 0.96 (d, J=5.2 Hz, 1H), 1.07 (d, J=5.2 Hz, 1H), 1.46 (s, 9H), 1.4-1.7 (m, 10H), 3.40 (m, 2H), 4.95 (s, 1H); MS (APCI) m/z 263 [M−H]−.

Workup

  1. temperaturecooled in an ice bath
  2. customto form
  3. waitAfter 1 hour
  4. temperaturecooling
  5. customtransferred to a separatory funnel
  6. extractionThe solution was extracted with ethyl acetate (3×400 mL)
  7. washThe combined organic layers were washed with brine (2×400 mL)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated under reduced pressure
  11. dissolutionThe residue was dissolved in ethyl acetate (300 mL)
  12. washwashed with brine (3×300 mL)
  13. dry with materialdried over sodium sulfate
  14. filtrationfiltered
  15. customevaporated

Sources & evidence

ORD record
ord-55bbe954fd054a2dac35d340b547f533
Source dataset
uspto-grants-2007_07
Patent number
US07250433B2

Reaction notes

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