Methanol → HCID 86703524, compound

Temperature

0 °C

To a stirred solution of methyl 2-fluoroadamantane-2-carboxylate (0.90 g, 4.20 mmol) (Zhurnal Organicheskoi Khimii, 1981, 17, 1642) in tetrahydrofuran (40 mL) was added methanol (0.24 mL, 5.90 mmol), followed by the addition of lithium borohydride solution (2.0 M in tetrahydrofuran, 5.3 mL, 10.60 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 15 minutes, at ambient temperature for 30 minutes and then at reflux for 1 hour. The reaction mixture was cooled to ambient temperature and poured in small portions into a cooled to 0° C. saturated ammonium chloride solution (25 mL) with stirring. The mixture was stirred at ambient temperature for 1 hour and extracted with ethyl acetate (3×70 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford (2-fluoroadamantan-2-yl)methanol (0.69 g, 88%) as colorless solid: MS (ES+) m/z 223.2 (M+39).

1. temperatureat reflux for 1 hour
2. temperatureThe reaction mixture was cooled to ambient temperature
3. additionpoured in small portions into
4. stirringwith stirring
5. stirringThe mixture was stirred at ambient temperature for 1 hour
6. extractionextracted with ethyl acetate (3×70 mL)
7. washThe combined organic layers were washed with brine (100 mL)
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-d787d7cee4b34874b0b3a9c06ac53738

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952169B2