1-Heptanol, 7-bromo- → 2-(7-[2-(2,3-Difluoro-phenyl)-ethoxy]-heptyloxy)-tetrahydro-pyran

Participants

Reaction Steps

The title compound, m/e=413.5 ([M−H]−), was produced in analogy with example 54, steps 1 to 6. Thus, 7-bromo-1-heptanol was protected in step 1, leading to 2-(7-bromo-heptyloxy)-tetrahydro-pyran, which was reacted in step 2 with 2-(2,3-difluorophenoxy)-ethanol, affording 2-(7-[2-(2,3-difluoro-phenyl)-ethoxy]-heptyloxy)-tetrahydro-pyran, which after deprotection in step 3 gave 7-[2-(2,3-difluoro-phenyl)-ethoxy]-heptan-1-ol. This was oxidized in step 4 to 7-[2-(2,3-difluoro-phenyl)-ethoxy]-heptanoic acid, which was coupled in step 5 with (R)-3-amino-4-dimethylamino-butyric acid benzyl ester dihydrochloride, leading to (R)-3-{7-[2-(2,3-difluoro-phenyl)-ethoxy]-heptanoylamino}-4-dimethylamino-butyric acid benzyl ester, which was hydrogenated in step 6.

Provenance & Evidence