Dimethylformamide → 2-Chloro-5-formyl-N-(tricyclo [3.3.1.13,7]dec-1-ylmethyl)-benzamide

Temperature

-78 °C

A solution of 5-bromo-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (3.25 g, Example 23a) in anhydrous tetrahydrofuran (150 ml) was cooled to −78° C. under a nitrogen atmosphere. A solution of methyllithium (1.4M in diethyl ether, 6.1 ml) was added over 2 min. The mixture was stirred at −78° C. for 10 min, then a solution tert-butyllithium (1.7M in pentane, 10.0 ml) was added dropwise. The mixture was stirred at −78° C. for a further 10 min, then dimethylformamide (1.0 ml) was added. The resulting solution was stirred at −78° C. for 30 min., quenched with saturated aqueous ammonium chloride solution (100 ml) and extracted with ethyl acetate. The combined extracts were dried over anhydrous magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to give the subtitle compound as a solid (2.76 g).

1. stirringThe mixture was stirred at −78° C. for a further 10 min
2. stirringThe resulting solution was stirred at −78° C. for 30 min.
3. customquenched with saturated aqueous ammonium chloride solution (100 ml)
4. extractionextracted with ethyl acetate
5. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationthe filtrate concentrated under reduced pressure

ORD record

ord-3846feb1d6d84f8a8c4c57c4af289504

Source dataset

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06492355B1