Dibromodifluoromethane → (2S,3E)-1,4-diphenylbut-3-en-2-amine

552.7 mg (9.85 mmol) of potassium hydroxide were dissolved in methanol, adsorbed onto 1.1 g of neutral aluminium oxide and then dried under high vacuum. To a solution of 240 mg (0.82 mmol) of (2S)-1-(benzylsulphonyl)-3-phenylpropan-2-amine and 1.56 g of the potassium hydroxide on aluminium oxide thus prepared in 6.2 ml of n-butanol were added dropwise, at 5-10° C., 307 μl (3.3 mmol) of dibromodifluoromethane. The reaction mixture was stirred at RT for 2 h, then filtered through Celite, and the residue was washed thoroughly with dichloromethane. The filtrate was concentrated and the resulting residue was dried under reduced pressure. The crude product thus obtained was purified by means of preparative HPLC. 98 mg (35% of theory) of the title compound were obtained with an E/Z diastereomer ratio of 4:1.

1. customdried under high vacuum
2. additionwere added dropwise, at 5-10° C.
3. filtrationfiltered through Celite
4. washthe residue was washed thoroughly with dichloromethane
5. concentrationThe filtrate was concentrated
6. customthe resulting residue was dried under reduced pressure
7. customThe crude product thus obtained
8. customwas purified by means of preparative HPLC

ORD record

ord-2a756f9b74224f8093ddb93c0dac91ed

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08992932B2