Pentane → α-(1,1-Dimethylethyl)-5-fluoro-2-pyridinemethanamine

Temperature

0 °C

To an ice-cooled solution of 5-fluoropicolinaldehyde (0.10 g, 0.799 mmol) in THF (5 mL) was added a 1.0 M THF solution of LiHMDS (0.879 mL, 0.879 mmol). The violet solution was stirred at 0° C. for 20 min then cooled to −78° C. A 1.7 M pentane solution of tert-butyllithium (0.470 mL, 0.799 mmol) was added dropwise. Stirring was continued for 1.5 h at −78° C. The reaction was carefully quenched by addition of water (20 mL). The layers were separated, and the aqueous layer was extracted with ethyl acetate. The combined organics were washed with brine, dried over anhydrous MgSO4, filtered, then concentrated to give the title compound (123 mg) as an orange oil. LCMS m/z=183.2 [M+H]+.

1. temperaturethen cooled to −78° C
2. stirringStirring
3. waitwas continued for 1.5 h at −78° C
4. customThe reaction was carefully quenched by addition of water (20 mL)
5. customThe layers were separated
6. extractionthe aqueous layer was extracted with ethyl acetate
7. washThe combined organics were washed with brine
8. dry with materialdried over anhydrous MgSO4
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-8713a1c2dcec4f1ebb079e4de7266987

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778950B2