Iodine → HCID 66660749, compound

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).

1. filtrationThe reaction mixture was filtered through Celite
2. washwashed with acetonitrile (5 mL)
3. temperaturethe mixture warmed to 50° C. for 10 minutes
4. stirringthe reaction mixture was stirred at 50° C. for 6 hours
5. customThe layers were separated
6. dry with materialthe organic layer was dried with Na2SO4
7. filtrationfiltered
8. concentrationconcentrated
9. customThe concentrate was purified by flash chromatography on SiO2
10. washeluting with 5% methanol in CH2Cl2 (0.1% NH4OH) isocratically

ORD record

ord-7ab2cc27f56b47cbbc4a6e899ea5d043

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08058293B2