Tetrahydrofuran → HCID 15542675, compound

HRID 2269853Notes

Reaction equation

HRID 2269853 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:54]=[C:55]([O:59][CH3:60])[C:56]=1[O:57][CH3:58])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:27][CH2:28][N:29]2[CH2:34][CH2:33][CH:32]([C:35]([C:37]3[N:41]([CH2:42][C:43]4[CH:48]=[CH:47][C:46]([F:49])=[CH:45][CH:44]=4)[C:40]4[CH:50]=[CH:51][CH:52]=[CH:53][C:39]=4[N:38]=3)=[O:36])[CH2:31][CH2:30]2)([C:13]2[CH:18]=[CH:17][C:16]([O:19][Si](C(C)(C)C)(C)C)=[CH:15][CH:14]=2)[CH2:9]1)=[O:7].C1COCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl>[CH3:60][O:59][C:55]1[CH:54]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:56]=1[O:57][CH3:58])[C:6]([N:8]1[CH2:12][CH2:11][C:10]([CH2:27][CH2:28][N:29]2[CH2:30][CH2:31][CH:32]([C:35]([C:37]3[N:41]([CH2:42][C:43]4[CH:44]=[CH:45][C:46]([F:49])=[CH:47][CH:48]=4)[C:40]4[CH:50]=[CH:51][CH:52]=[CH:53][C:39]=4[N:38]=3)=[O:36])[CH2:33][CH2:34]2)([C:13]2[CH:14]=[CH:15][C:16]([OH:19])=[CH:17][CH:18]=2)[CH2:9]1)=[O:7]

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 2724141Tetrabutylammonium FluorideHCID 155428991-(3,4,5-trimethoxy-benzoyl)-3-[2-[4-[1-(4-fluoro-benzyl)-1 H-benzoimidazole-2-carbonyl]-piperidin-1-yl]-ethyl]-3-(4-(t-butyldimethylsilyloxy)-phenyl)-pyrrolidine

Product 1

HCID 15542675HCID 15542675, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 1-(3,4,5-trimethoxy-benzoyl)-3-[2-[4-[1-(4-fluoro-benzyl)-1 H-benzoimidazole-2-carbonyl]-piperidin-1-yl]-ethyl]-3-(4-(t-butyldimethylsilyloxy)-phenyl)-pyrrolidine (6 mmol) and THF (20 mL). Cool using an ice bath. Add dropwise, a 1 M THF solution of tetrabutylammonium fluoride (7 mL). After 30 minutes, concentrate in vacuo to obtain a residue. Combine dichloromethane (50 mL) and the residue. Extract with water (3×15 mL), dry the organic layer over Na2SO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph on silica gel to obtain the title compound.

Workup

  1. temperatureCool
  2. additionAdd dropwise
  3. concentrationconcentrate in vacuo
  4. customto obtain a residue
  5. extractionExtract with water (3×15 mL)
  6. dry with materialdry the organic layer over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customto obtain a residue

Sources & evidence

ORD record
ord-bde5fb392ea249559a508d64cbfb6fdd
Source dataset
uspto-grants-2001_12
Patent number
US06329392B1

Reaction notes

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