4-Iodophenol → (2S, 4S)-1-N-Dodecyl-4-(4-iodophenoxy)pyrrolidine-2-carboxylic acid, methyl ester

HRID 1700901Notes

Reaction equation

HRID 1700901 reaction equation
[CH2:1]([N:13]1[CH2:17][C@H:16]([OH:18])[CH2:15][C@H:14]1[C:19]([O:21][CH3:22])=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[I:23][C:24]1[CH:29]=[CH:28][C:27](O)=[CH:26][CH:25]=1.C(N(CCOC1C=CC(CCC(OC)=O)=CC=1)C)CCCCCCCCCCC>>[CH2:1]([N:13]1[CH2:17][C@@H:16]([O:18][C:27]2[CH:28]=[CH:29][C:24]([I:23])=[CH:25][CH:26]=2)[CH2:15][C@H:14]1[C:19]([O:21][CH3:22])=[O:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 3

HCID 108944-IodophenolHCID 229499593-[4-[2-(N-dodecyl-N-methylamino)ethoxy]phenyl]propanoic acid methyl esterHCID 86757128(2S, 4R)-1-N-Dodecyl-4-hydroxypyrrolidine-2-carboxylic acid, methyl ester

Product 1

HCID 86757129(2S, 4S)-1-N-Dodecyl-4-(4-iodophenoxy)pyrrolidine-2-carboxylic acid, methyl esterYield 86.8%

Procedure

(2S, 4R)-1-N-Dodecyl-4-hydroxypyrrolidine-2-carboxylic acid, methyl ester (1.75 g, 7.94 mmol) and 4-iodophenol (2.26 g, 7.22 mmol) were reacted under Mitsunobu conditions as described in the preparation of 3-[4-[2-(N-Dodecyl-N-methylamino)ethoxy]phenyl]propanoic acid, methyl ester. The residue was chromatographed on silica gel (hexane/ethyl acetate 15:1 to 10:1) to afford the title compound (3.23 g, 79%) as a white solid. [a]D=−30.80 (c 1.0, CHCl3)

Workup

  1. customThe residue was chromatographed on silica gel (hexane/ethyl acetate 15:1 to 10:1)

Sources & evidence

ORD record
ord-64932ca122b347f899997b0ff9071176
Source dataset
uspto-grants-2002_02
Patent number
US06350892B1

Reaction notes

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