反应详情

(1S,5S)-3-Benzenesulfonyl-1-(3,4-dichlorophenyl)-3-methylsulfanyl-bicyclo[3.1.0]hexane (3.5 g, 8.4 mmol), methanol (15 mL) and concentrated hydrochloric acid (3 mL) were heated to reflux for 7 hours. The reaction was monitored by TLC (ethyl acetate/hexane(20:80)). The reaction mixture was concentrated under reduced pressure to remove methanol. The pH of the reaction mass was adjusted to 8-9 with saturated sodium bicarbonate solution. The aqueous layer was extracted with diethyl ether (300 mL). The organic layer was washed with water, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to yield 3 g of crude oil, which was purified by preparative HPLC to give 900 mg (45%) of 99% pure product. 1H NMR δ(300 MHz,CDCl3) 0.68-0.70 (1H,t, J=4 Hz), 1.25-1.35 (1H,m), 1.94-2.15 (1H,m), 2.36-2.42 (1H, d, J=10 Hz), 2.59-2.66 (1H,d,J=10 Hz), 2.83-2.89 (2H,m), 6.99-7.03 (1H,dd,J=9,3 Hz), 7.25-7.26 (1H,d,J=3 Hz), 7.36-7.39 (1H,d,J=9 Hz). 13CNMR(CDCl3)δ: 215.28, 143.49, 132.57, 130.4, 130.07, 128.09, 125.41, 45.35, 42.08, 27.20, 23.31, 22.23.

1. temperatureto reflux for 7 hours
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. customto remove methanol
4. extractionThe aqueous layer was extracted with diethyl ether (300 mL)
5. washThe organic layer was washed with water
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. customevaporated under reduced pressure
9. customto yield 3 g of crude oil, which
10. customwas purified by preparative HPLC