Pyridine → HCID 59779131, compound

To a stirred solution of 5-naphthalen-1-yl-bicyclo[3.1.0]hexan-2-ol (1.00 g, 4.46 mmol) in dichloromethane (40 mL) was added pyridine (0.50 mL, 6.24 mmol, 1.4 eq.) followed by Dess-Martin periodinane (2.27 g, 5.35 mmol, 1.2 eq.) and the reaction mixture was warmed to room temperature and stirred for 3 h. To the reaction mixture was added 3 drops of water and the reaction mixture was left to stir for a further 0.5 h. The reaction mixture was quenched with saturated aqueous sodium bicarbonate (100 mL) followed by saturated aqueous sodium sulphite (100 mL) and extracted with dichloromethane (3×200 mL). The combined organic layers were dried over magnesium sulphate and concentrated in vacuo to afford the desired compound as a yellow oil. The crude material was purified by flash chromatography (SiO2, ethyl acetate:petroleum ether 40-60; 30%:70%) to afford the desired compound as a yellow oil (0.71 g, 72%). 1H NMR (400 MHz, CDCl3) δ ppm 1.59-1.61 (1H, m, CH), 1.68-1.70 (2H, m, CH2), 2.21-2.23 (1H, m, CH), 2.24-2.40 (3H, m, CH and CH2), 7.44-7.54 (4H, m, ArH), 7.79 (1H, d, J 8.0 Hz, ArH), 7.88 (1H, d, J 8.0 Hz, ArH), 8.17 (1H, d, J 8.0 Hz, ArH).

1. waitthe reaction mixture was left
2. stirringto stir for a further 0.5 h
3. customThe reaction mixture was quenched with saturated aqueous sodium bicarbonate (100 mL)
4. extractionextracted with dichloromethane (3×200 mL)
5. dry with materialThe combined organic layers were dried over magnesium sulphate
6. concentrationconcentrated in vacuo

ORD record

ord-9687129881e14c079a05ff62e9783e7b

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08138377B2