Cyclohexene oxide → HCID 16735232, compound

To anhydrous magnesium perchlorate (12.93 g, 53.3 mmol) was added a solution of cyclohexene oxide (6.1 mL, 58.6 mmol) in anhydrous acetonitrile (25 mL) and the resulting mixture was stirred at room temperature for 20 min. Then a solution of thiazolidine (5.16 g, 55.0 mmol) in anhydrous acetonitrile was added and the reaction mixture was heated at 35° C. for 16 hours. The reaction mixture was concentrated in vacuo and the residue was partitioned between water (350 mL) and diethyl ether (350 mL). The aqueous layer was separated and extracted once more with diethyl ether (350 mL). The combined organic extracts were dried over sodium sulfate and concentrated in vacuo to provide the crude product. The crude aminoalcohol was purified by dry-column chromatography with a mixture of ethyl acetate-hexanes (1:1, v/v) as eluent to yield 4.83 g (47% yield) of the title compound.

1. temperaturethe reaction mixture was heated at 35° C. for 16 hours
2. concentrationThe reaction mixture was concentrated in vacuo
3. customthe residue was partitioned between water (350 mL) and diethyl ether (350 mL)
4. customThe aqueous layer was separated
5. extractionextracted once more with diethyl ether (350 mL)
6. dry with materialThe combined organic extracts were dried over sodium sulfate
7. concentrationconcentrated in vacuo
8. customto provide the crude product
9. customThe crude aminoalcohol was purified by dry-column chromatography with a mixture of ethyl acetate-hexanes (1:1

ORD record

ord-81c4418d237b4a4ea6ce2aa799d6db25

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08008342B2