Ethyl orthoformate → 2-Chloro-5-methylamino-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Temperature

120 °C

Amino amide from Example 55 (0.12 g) was dissolved in triethylorthoformate (1.07 ml) and heated at 120° C. for three hours. The triethylorthoformate was removed by vacuum distillation. The residue was dissolved in ethanol (5 ml). The solution was cooled to 0° C. under nitrogen, sodium borohydride (0.104 g) was added and the mixture refluxed for three hours at 90° C. The ethanol was removed under reduced pressure, water (20 ml) was added to the residue, the product was extracted into ethyl acetate (3×50 ml), dried over magnesium sulphate and concentrated under reduced pressure. The crude product was purified by silica gel chromatography eluting with dichloromethane:ethyl acetate (1:1) to give the title compound as a white solid (0.04 g).

1. customThe triethylorthoformate was removed by vacuum distillation
2. dissolutionThe residue was dissolved in ethanol (5 ml)
3. temperatureThe solution was cooled to 0° C. under nitrogen
4. additionsodium borohydride (0.104 g) was added
5. temperaturethe mixture refluxed for three hours at 90° C
6. customThe ethanol was removed under reduced pressure, water (20 ml)
7. additionwas added to the residue
8. extractionthe product was extracted into ethyl acetate (3×50 ml)
9. dry with materialdried over magnesium sulphate
10. concentrationconcentrated under reduced pressure
11. customThe crude product was purified by silica gel chromatography
12. washeluting with dichloromethane:ethyl acetate (1:1)

ORD record

ord-d516a8b912d4453ebf8f5d880f363e54

Source dataset

uspto-grants-2001_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06201024B1