Tetrahydrofuran → HCID 15142921, compound

Temperature

5 °C

Stirred mixture of trans-1,2-diaminocyclohexane (10.0 g, 87.6 mmol), THF (150 mL) water (120 mL) and potassium carbonate (40 g) was cooled to 5° C. and treated with ethyl chloroformate (35 mL, 39.9 g, 367 mmol). The mixture was stirred at ambient temperature for 4 hours, the upper layer was separated and the aqueous phase was extracted with THF (70 mL). The combined THF extract was evaporated to dryness. The residue was dissolved in dichloromethane. The solution was dried over potassium carbonate, filtered and evaporated to dryness. The obtained white solid was slurried in ether (70 mL), filtered, washed with pentane (2×80 mL) and dried in an oven at 90° C. for 2 hours to give 22.03 g (97% yield) of trans-1,2-bis(ethoxycarbonylamino)cyclohexane as a snow-white solid.

1. stirringThe mixture was stirred at ambient temperature for 4 hours
2. customthe upper layer was separated
3. extractionthe aqueous phase was extracted with THF (70 mL)
4. extractionThe combined THF extract
5. customwas evaporated to dryness
6. dissolutionThe residue was dissolved in dichloromethane
7. dry with materialThe solution was dried over potassium carbonate
8. filtrationfiltered
9. customevaporated to dryness
10. filtrationfiltered
11. washwashed with pentane (2×80 mL)
12. customdried in an oven at 90° C. for 2 hours

ORD record

ord-ec6e7f641bb84c04b1d64bc758adf879

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07399859B1