Sodium borohydride → HCID 44546740, compound

To a solution of Compound 15 (˜110 mmol) in methanol (600 mL), sodium borohydride (5.4 g, 142.8 mmol) was added in portions at 0° C. The reaction mixture was first stirred overnight while warming up to room temperature. The reaction mixture was concentrated under reduced pressure. The residue was diluted with water (200 mL) and the solution was extracted with methylene chloride (3×300 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated to dryness under reduced pressure to afford the crude desired product Compound 16 (42.6 g) as a yellow oil, which was used without further purification in the next step: 1H NMR (300 MHz, CDCl3) δ 7.86-7.79 (m, 4H), 7.52-7.38 (m, 5H), 7.28-7.15 (m, 2H), 4.93 (dd, J=9.5, 4.4 Hz, 1H), 4.05 (s, 1H), 3.71 (d, J=13.3 Hz, 1H), 3.52 (d, J=13.3 Hz, 1H), 2.72-2.61 (m, 2H), 2.34 (s, 3H).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additionThe residue was diluted with water (200 mL)
3. extractionthe solution was extracted with methylene chloride (3×300 mL)
4. dry with materialThe combined organic extracts were dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated to dryness under reduced pressure

ORD record

ord-73400928e68d48c292fc2f6ba7e55e4f

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08420811B2