Iodine → HCID 66660749, compound

Participants

Reaction Steps

A mixture of tert-butyl 2-aminoethylcarbamate (5.9 g, 37 mmol) and 3,3-dimethylbutanal (4.9 mL 95%, 37 mmol) in 30 mL of dry acetonitrile with 4 g of 4 Å (8-12 mesh beads) molecular sieves was stirred at ambient temperature for 24 hours. The mixture was filtered through Celite and washed with 5 mL of acetonitrile. 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 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 the solvent removed. The residue was chromatographed by equilibrating the column with CH2Cl2, loading the sample, and eluting with 5% methanol in CH2Cl2 (0.1% NH4OH) isocratically to afford the title compound (3.5 g, 11.7 mmol, 32% yield). MS (DCI/NH3) m/z 300.2 (M+H)+. 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 1.31 (s, 9 H) 1.42 (s, 9 H) 3.57 (q, J=6.78 Hz, 2 H) 4.26 (t, J=6.95 Hz, 2 H) 5.63 (t, J=5.76 Hz, 1 H) 6.58 (s, 1 H).

Provenance & Evidence