Acetic Acid → HCID 68905599, compound

Temperature

-78 °C

Anhydrous cerium chloride (6.4 g) was suspended in tetrahydrofuran (50 ml), and the suspension was cooled to −78° C. in an argon atmosphere. A methyllithium solution (1.14N diethyl ether solution, 22.5 ml) was added to the suspension, and the mixture was stirred at −78° C. for 30 minutes. A tetrahydrofuran solution (50 ml) of (±)-cis-N1,N2-bis(benzyloxycarbonyl)-4-oxo-1,2-cyclohexanediamine (3.0 g) was added dropwise at −78° C., and the mixture was stirred for 30 minutes. The reaction mixture was poured into a 3% aqueous solution (100 ml) of acetic acid, and diethyl ether (50 ml) was added to stir the mixture at room temperature for 10 minutes. The reaction mixture was extracted with ethyl acetate, and the resultant organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified twice by medium-pressure column chromatography on silica gel (methanol:chloroform=0:100-1:19) to obtain the title compound (Stereoisomer A) (780 mg) as a colorless foamy compound and the title compound (Stereoisomer B) (1.1 g) as white powder.

1. stirringthe mixture was stirred for 30 minutes
2. additionwas added
3. stirringto stir the mixture at room temperature for 10 minutes
4. extractionThe reaction mixture was extracted with ethyl acetate
5. washthe resultant organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline
6. dry with materialdried over anhydrous sodium sulfate
7. distillationThe solvent was distilled off under reduced pressure
8. customthe residue was purified twice by medium-pressure column chromatography on silica gel (methanol:chloroform=0:100-1:19)

ORD record

ord-f3ca5608aca24d19a8e72ef543e4b695

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07935824B2