Ammonium Chloride → HCID 178445700, compound

Temperature

-78 °C

To a mixture of 1.9 M sodium hexamethyldisilazane solution (in tetrahydrofuran, 2.1 ml) and anhydrous tetrahydrofuran (10 ml) was added n-propyltriphenyl-phosphonium bromide (1.52 g) at room temperature, and the mixture was stirred for 30 minutes. The reaction mixture was cooled to −78° C., and then a solution of t-butyl cis-4-formylcyclohexylcarbamate (900 mg) in anhydrous tetrahydrofuran (5 ml) was added thereto. The reaction mixture was gradually warmed to 25° C. and stirred overnight. To the reaction mixture was added saturated aqueous ammonium chloride, and the mixture was extracted with ethyl acetate, the organic layer was washed with brine, dried over sodium sulfate, and then the solvent was removed in vacuo. After diethyl ether was added to the residue, the precipitate was filtered off and then the filtrate was concentrated under reduced pressure. The residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate) to give 405 mg of t-butyl cis-4-[(Z)-1-butenyl]cyclohexylcarbamate.

1. temperatureThe reaction mixture was gradually warmed to 25° C.
2. stirringstirred overnight
3. extractionthe mixture was extracted with ethyl acetate
4. washthe organic layer was washed with brine
5. dry with materialdried over sodium sulfate
6. customthe solvent was removed in vacuo
7. additionAfter diethyl ether was added to the residue
8. filtrationthe precipitate was filtered off
9. concentrationthe filtrate was concentrated under reduced pressure
10. customThe residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate)

ORD record

ord-b4809406406d4016ae27904307cd1dfe

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07767854B2