Reaktion #167143

Reaktionsgleichung

2-[5-(4′-{2-[1-(5,5,5-trifluoro-2-methoxycarbonylamino-pentanoyl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester

trifluoroacetic acid

→

pyrrolidine

Ausbeute 92.3%

[4,4,4-Trifluoro-1-(2-{5-[4′-(2-pyrrolidin-2-yl-3H-imidazol-4-yl)-biphenyl-4-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-butyl]-carbamic acid methyl ester

Ausbeute 92.3%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenthoroughly concentrated
2. 2
   workup.DISSOLUTIONThe resulting residue was dissolved in dichloromethane
3. 3
   Waschenwashed three times with saturated aqueous NaHCO3 solution
4. 4
   TrocknenThe organic layer was dried (MgSO4)
5. 5
   Einengenconcentrated

Vorschrift

To a solution of 2-[5-(4′-{2-[1-(5,5,5-trifluoro-2-methoxycarbonylamino-pentanoyl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-biphenyl-4-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester (340 mg, 0.46 mmol) in dichloromethane (5 mL) was added trifluoroacetic acid (1 mL). The reaction was stirred at room temperature for 3 hours and then thoroughly concentrated. The resulting residue was dissolved in dichloromethane and washed three times with saturated aqueous NaHCO3 solution. The organic layer was dried (MgSO4), and concentrated to give the crude free pyrrolidine (270 mg, 92%), which was clean enough to use without further purification. LCMS-ESI+: calculated for C33H36F3N7O3: 635.28; observed [M+1]+: 636.17.

Quelle