3-Phenoxy 1-propanol → HCID 66875177, compound

HRID 1799655Notes

Reaction equation

HRID 1799655 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10].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(CCCO)[C:28]1C=CC=CC=1>>[C:6]1([CH2:7][CH2:8][CH2:9][O:10][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[CH:5]=[CH:4][CH:3]=[CH:2][CH:28]=1

Participants

4

Reactant 3

HCID 803193-Phenoxy 1-propanolHCID 1626071-Octanol, 8-bromo-HCID 1709162H-Pyran, 2-[(8-bromooctyl)oxy]tetrahydro-

Product 1

HCID 66875177HCID 66875177, compound

Procedure

The title compound, m/e=405.7 ([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 3-phenoxypropanol, affording 2-(8-(3-phenyl-propoxy)-octyloxy)-tetrahydro-pyran, which after deprotection in step 3 gave 8-(3-phenyl-propoxy)-octan-1-ol. This was oxidized in step 4 to 8-(3-phenyl-propoxy)-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-(3-phenyl-propoxy)-octanoylamino]-butyric acid benzyl ester, which was hydrogenated in step 6.

Sources & evidence

ORD record
ord-89c7e919c1874409a2888784c1ef4da8
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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