methyl 6-(trifluoromethyl)nicotinate → 6-(Trifluoromethyl)pyridine-3-methanol

To a solution of Example 85A (4.1 g, 20.0 mmol) in 100 mL of methanol was added 7.6 g of NaBH4 in portions at 0° C. The resulting mixture was stirred at room temperature overnight, then quenched with water (100 mL). Most of the methanol was removed in vacuo. The residue was extracted with ethyl acetate (100 mL×3). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The crude product was purified by silica gel column (petroleum ether:ethyl acetate=5:1) to afford the title compound (2.8 g, 79.1%). 1H NMR (400 MHz, CDCl3): δ 8.68 (s, 1H), 7.92 (d, J=8.0 Hz, 1H), 7.70 (s, J=8.0 Hz, 1H), 4.84 (s, 2H), 2.48 (s, br, 1H).

1. customquenched with water (100 mL)
2. customMost of the methanol was removed in vacuo
3. extractionThe residue was extracted with ethyl acetate (100 mL×3)
4. dry with materialThe combined organic layers were dried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe crude product was purified by silica gel column (petroleum ether:ethyl acetate=5:1)

ORD record

ord-d589eb3361c44b1cb0aafb74893caef2

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772500B2