Iodoethane → tert-Butyl (3-ethylpyridin-2-yl)carbamate

Temperature

-78 °C

2-t-Butoxycarbonylaminopyridine (10 g, 51.5 mmol) was dissolved in tetrahydrofuran (80 mL), and cooled to -78° C. N-butyllithium (80 mL of 1.49M in hexanes, 120 mmol) was added dropwise over a period of 1 h. After stirring for an additional 15 min at -78° C. and then for 2.5 hours at -10° C., the solution was then recooled back down to -78° C. and iodoethane (77.2 mmol, 6.18 mL) was added dropwise over a period of 15 min via syringe. The solution was allowed to warm to room temperature. The reaction was quenched with 100 mL of a saturated ammonium chloride and extracted with ethyl acetate (3×). The organic layers were collected, dried over magnesium sulfate, and concentrated. The resulting solid was purified by flash chromatography on silica gel (25% ethyl acetate/hexanes) to provide the 4.9 g (43%) of the titled product as a light brown solid:

1. waitfor 2.5 hours at -10° C.
2. customwas then recooled back down to -78° C.
3. temperatureto warm to room temperature
4. customThe reaction was quenched with 100 mL of a saturated ammonium chloride
5. extractionextracted with ethyl acetate (3×)
6. customThe organic layers were collected
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated
9. customThe resulting solid was purified by flash chromatography on silica gel (25% ethyl acetate/hexanes)

ORD record

ord-efaf9e6afdeb4ef2bc478ffd3a61304d

Source dataset

uspto-grants-1997_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05593993