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

HRID 1799661Notes

Reaction equation

HRID 1799661 reaction equation
BrCCCCC[CH2:7][CH2:8][OH:9].Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1.[F:25][C:26]1[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:27]=1OCCO>>[F:25][C:26]1[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:27]=1[CH2:7][CH2:8][O:9][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1

Participants

4

Reactant 3

HCID 662841-Heptanol, 7-bromo-HCID 5590082-[(7-Bromoheptyl)oxy]tetrahydro-2H-pyranHCID 220365312-(2,3-Difluorophenoxy)-ethanol

Product 1

HCID 668751352-(7-[2-(2,3-Difluoro-phenyl)-ethoxy]-heptyloxy)-tetrahydro-pyran

Procedure

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.

Sources & evidence

ORD record
ord-e7d00b379d174c33a4517077411b6695
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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