Phenoxyethanol → 2-(8-(2-Phenoxy-ethoxy)-octyloxy)-tetrahydro-pyran

HRID 1799656Notes

Reaction equation

HRID 1799656 reaction equation
BrCCCCCCCCO.Br[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1.[O:27]([CH2:34][CH2:35][OH:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[O:27]([CH2:34][CH2:35][O:36][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 3

HCID 31236PhenoxyethanolHCID 1626071-Octanol, 8-bromo-HCID 1709162H-Pyran, 2-[(8-bromooctyl)oxy]tetrahydro-

Product 1

HCID 668748132-(8-(2-Phenoxy-ethoxy)-octyloxy)-tetrahydro-pyran

Procedure

The title compound, m/e=407.6 ([M−H]−), was produced in analogy with example 54, steps 1 to 6. Thus, 8-bromo-1-octanol was protected in step 1, leading to 2-(8-bromo-octyloxy)-tetrahydro-pyran, which was reacted in step 2 with 2-phenoxyethanol, affording 2-(8-(2-phenoxy-ethoxy)-octyloxy)-tetrahydro-pyran, which after deprotection in step 3 gave 8-(2-phenoxy-ethoxy)-octan-1-ol. This was oxidized in step 4 to 8-(2-phenoxy-ethoxy)-octanoic acid, which was coupled in step 5 with (R)-3-amino-4-dimethylamino-butyric acid benzyl ester dihydrochloride, leading to (R)-4-dimethylamino-3-[8-(2-phenoxy-ethoxy)-octanoylamino]-butyric acid benzyl ester, which was hydrogenated in step 6.

Sources & evidence

ORD record
ord-79b300ad2b934a34b47f140ef6f4db41
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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