Borane;tetrahydrofuran → HCID 67172357, compound

Participants

Reaction Steps

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)].

Provenance & Evidence