Dabco → 1-[4-(4-{1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}phenoxymethyl)benzyl]-4-aza-1-azoniabicyclo[2.2.2]octane bromide

HRID 2105724Notes

Reaction equation

HRID 2105724 reaction equation
[Br:1][CH2:2][C:3]1[CH:39]=[CH:38][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[N:18]([C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[C:17](=[O:26])[CH:16]3[CH2:27][CH2:28][CH:29]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[OH:30])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[N:40]12[CH2:47][CH2:46][N:43]([CH2:44][CH2:45]1)[CH2:42][CH2:41]2>C1(C)C=CC=CC=1>[Br-:1].[F:25][C:22]1[CH:21]=[CH:20][C:19]([N:18]2[C:17](=[O:26])[CH:16]([CH2:27][CH2:28][CH:29]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[OH:30])[CH:15]2[C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:7][C:6]3[CH:5]=[CH:4][C:3]([CH2:2][N+:40]45[CH2:47][CH2:46][N:43]([CH2:44][CH2:45]4)[CH2:42][CH2:41]5)=[CH:39][CH:38]=3)=[CH:14][CH:13]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 9237DabcoHCID 210831904-[4-(4-Bromomethylbenzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]azetidin-2-one

Product 1

HCID 210831571-[4-(4-{1-(4-Fluorophenyl)-3-[3-(4-fluorophenyl)-3-hydroxypropyl]-4-oxoazetidin-2-yl}phenoxymethyl)benzyl]-4-aza-1-azoniabicyclo[2.2.2]octane bromide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

180 mg of (12) and 300 mg of 1,4-diazabicyclo[2.2.2]octane (DABCO) were dissolved in 5 ml of toluene and stirred at 80° C. for 90 min. After the reaction ended, the mixture was allowed to cool and the colorless solid was filtered off with suction. This gave 195 mg of product (13) of molecular weight 704.66 (C38H40BrF2N3O3); MS (ESI): 624.30 (MH+).

Workup

  1. temperatureto cool
  2. filtrationthe colorless solid was filtered off with suction

Sources & evidence

ORD record
ord-b857ea4dfba647ad9314131aadf93523
Source dataset
uspto-grants-2009_08
Patent number
US07579339B2

Reaction notes

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