Tetrabutylammonium Fluoride → HCID 91506330, compound

HRID 220315Notes

Reaction equation

HRID 220315 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:26][CH2:27][CH2:28][N:29]([CH3:52])[CH2:30][CH2:31][C@:32]3([O:46][C:47](=[O:51])[CH:48]([CH3:50])[CH3:49])[CH2:37][C@H:36]4[CH2:38][CH2:39][C@@H:33]3[CH:34]=[C:35]4[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[N:10](COCC[Si](C)(C)C)[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(Cl)Cl>[C:12]1([C:11]2[N:10]=[C:9]([CH2:26][CH2:27][CH2:28][N:29]([CH3:52])[CH2:30][CH2:31][C@:32]3([O:46][C:47](=[O:51])[CH:48]([CH3:50])[CH3:49])[CH2:37][C@H:36]4[CH2:38][CH2:39][C@@H:33]3[CH:34]=[C:35]4[C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[NH:8][C:7]=2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 90975193HCID 90975193, compound

Product 1

HCID 91506330HCID 91506330, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 30 mg of rac-isobutyric acid (1R*,2R*,4R*)-2-[2-({3-[4,5-diphenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-propyl}-methyl-amino)-ethyl]-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl ester in 0.5 mL of anh. THF was added dropwise 0.2 mL of a 1M solution of TBAF in THF. The reaction mixture was refluxed for 6 h, diluted with DCM and washed with sat.-NaHCO3. The organic phase was dried over anh. Na2SO4 and concentrated in vacuo. The resulting crude material was purified by CC using EtOAc/MeOH/NEt3 from 100/0/1 to 90/10/1 as eluant to yield 14 mg of rac-isobutyric acid (1R*,2R*,4R*)-2-(2-{[3-(4,5-diphenyl-1H-imidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl ester as a yellowish solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 6 h
  2. washwashed with sat.-NaHCO3
  3. dry with materialThe organic phase was dried over anh. Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe resulting crude material was purified by CC

Sources & evidence

ORD record
ord-182b653a890a4220892311f25436b0c5
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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