Methanol → HCID 86703552, compound

Temperature

0 °C

To a solution of 1-methyl-4-(trifluoromethyl)cyclohexanecarboxylate (11.0 g, 49.00 mmol) in tetrahydrafuran (600 mL) was slowly added lithium borohydride solution (4.0 M in tetrahydrofuran, 37.0 mL, 147.00 mmol) and methanol (6.0 mL, 147.00 mmol) at 0° C. After stirring at 0° C. for 15 minutes, the reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was cooled to 0° C. and quenched with 25% aqueous ammonium chloride solution (100 mL), and extracted with ethyl acetate. The combined organic layers were washed with brine; dried over anhydrous magnesium sulfate; filtered and concentrated in vacuo. Purification of the residue by column chromatography (0 to 5% gradient ethyl acetate in hexanes) afforded the title compound (6.80 g, 72%) as a colorless oil): 1H NMR (300 MHz, CDCl3) δ 3.51 (s, 2H), 2.02-1.91 (m, 1H), 1.75-1.72 (m, 4H), 1.49-1.35 (m, 3H), 1.19-1.09 (m, 2H), 0.94 (s, 3H).

1. customat 0° C
2. stirringthe reaction mixture was stirred at ambient temperature for 16 hours
3. temperatureThe reaction mixture was cooled to 0° C.
4. customquenched with 25% aqueous ammonium chloride solution (100 mL)
5. extractionextracted with ethyl acetate
6. washThe combined organic layers were washed with brine
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customPurification of the residue by column chromatography (0 to 5% gradient ethyl acetate in hexanes)

ORD record

ord-eae1f9bf19eb4d08a4362e675c837ea7

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952169B2