Iodine → HCID 66660749, compound

Participants

Reaction Steps

tert-Butyl 2-aminoethylcarbamate (5.9 g, 37 mmol) and 3,3-dimethylbutanal (4.9 mL 95%, 37 mmol) were mixed in dry acetonitrile (30 mL) with 4 g of 4 Å (8-12 mesh beads) molecular sieves and stirred at room temperature for 24 hours. The reaction mixture was filtered through Celite and washed with acetonitrile (5 mL). Potassium thiocyanate (4.8 g, 49 mmol) was added and the mixture warmed to 50° C. for 10 minutes. Iodine (9.3 g, 37 mmol) was added and the reaction mixture was stirred at 50° C. for 6 hours. Acetonitrile (30 mL) was added followed by 10 mL of 20% Na2S2O5. The layers were separated and the organic layer was dried with Na2SO4, filtered, and concentrated. The concentrate was purified by flash chromatography on SiO2, equilibrating the column with CH2Cl2, loading the sample, and eluting with 5% methanol in CH2Cl2 (0.1% NH4OH) isocratically to provide the title compound (3.5 g, 11.7 mmol, 32% yield). MS (DCI/NH3) m/z 300.2 (M+H)+. 1H NMR (300 MHz, CDCl3) δ ppm 1.31 (s, 9H) 1.42 (s, 9H) 3.57 (q, J=6.78 Hz, 2H) 4.26 (t, J=6.95 Hz, 2H) 5.63 (t, J=5.76 Hz, 1H) 6.58 (s, 1H).

Provenance & Evidence