Sodium Bicarbonate → HCID 60124979, compound

To a stirred solution of 1.91 g (8.0 mmol) of 3-bromo-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one (J. Med. Chem. 2000, 43, 2049-2063) in 40 mL of ethanol under nitrogen cooled in an ice-bath was added 0.635 g (16.8 mmol, 2.1 equiv) of sodium borohydride. After three hours 32 mL of saturated sodium bicarbonate solution was added, and the mixture was concentrated under reduced pressure to remove the ethanol. The aqueous residue was diluted with 8 mL water and extracted with 2×80 mL of ethyl acetate. The combined extract was washed with 10 mL each of water and brine, dried over sodium sulfate, filtered, and concentrated to give product as a white crystalline solid. MS (m+1)=242.2; 1H NMR (400 MHz, CDCl3) 7.62 (s, 1H), 7.25 (m, 1H), 6.95 (d, 1H, J 8 Hz), 4.89 (d, 1H, J 9 Hz), 2.84 (m, 1H), 2.65 (d, 1H, J 12 Hz), 1.99 (m, 2H), 1.78 (m, 4H), 1.38 (m, 1H).

1. concentrationthe mixture was concentrated under reduced pressure
2. customto remove the ethanol
3. additionThe aqueous residue was diluted with 8 mL water
4. extractionextracted with 2×80 mL of ethyl acetate
5. extractionThe combined extract
6. washwas washed with 10 mL each of water and brine
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customto give product as a white crystalline solid

ORD record

ord-5faee6943e0246cca595c7eb151399c4

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07855201B2