Borane;tetrahydrofuran → HCID 67172357, compound

HRID 545300Notes

Reaction equation

HRID 545300 reaction equation
[N:1]1([C:10]2[CH:27]=[CH:26][C:13]([C:14]([N:16]3[CH2:20][CH2:19][C@H:18]([N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)[CH2:17]3)=O)=[CH:12][CH:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.B.C1COCC1.[ClH:34].CCOCC>C1COCC1.C(Cl)Cl>[ClH:34].[N:1]1([C:10]2[CH:27]=[CH:26][C:13]([CH2:14][N:16]3[CH2:20][CH2:19][C@H:18]([N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)[CH2:17]3)=[CH:12][CH:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 2723981Borane;tetrahydrofuranHCID 10953452Ether hydrochlorideHCID 24899976HCID 24899976, compound

Product 1

HCID 67172357HCID 67172357, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3′S)-1′-[4-(1H-benzimidazol-1-yl)benzoyl]-1,3′-bipyrrolidine (0.041 g, 0.113 mmol) in THF is treated with 1.0 M Borane-THF (0.098 g, 1.13 mmol) at room temperature, stirred for 12 hours and concentrated under vacuum. The resultant residue is dissolved in methanol, and treated with 1.0 M HCl-Et2O (0.004 g, 0.113 mmol), heated at reflux temperature for 3 hours and concentrated under vacuum to afford an oil residue. The residue is dissolved in CH2Cl2, washed with saturated NaHCO3 solution, dried over MgSO4 and concentrated in vacuo. Purification of the concentrate by flash column chromatography (silica, 2% NH4OH:MeOH:CH2Cl2 5:3:95), followed by treatment with ethereal HCl, provides the title product as a yellow solid, 0.036 g (65% yield), identified by NMR and mass spectral analyses. MS [347.2 m/e (M+H)].

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe resultant residue is dissolved in methanol
  3. temperatureheated
  4. temperatureat reflux temperature for 3 hours
  5. concentrationconcentrated under vacuum
  6. customto afford an oil residue
  7. washwashed with saturated NaHCO3 solution
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customPurification of the
  11. concentrationconcentrate by flash column chromatography (silica, 2% NH4OH:MeOH:CH2Cl2 5:3:95)

Sources & evidence

ORD record
ord-e1708b5e1aaa418785a900d6b9566319
Source dataset
uspto-grants-2011_05
Patent number
US07935719B2

Reaction notes

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