6-(4-Chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-carbaldehyde

The 4-chlorophenyl residue in the title compound, C20H16ClNO, is oriented at a dihedral angle of 53.6 (3)° towards the phenyl ring and 42.0 (9)° towards the pyrrole ring of the pyrrolizine template. The phenyl ring is oriented at a dihedral angle of 45.4 (4)° towards the pyrrole ring.

The 4-chlorophenyl residue in the title compound, C 20 H 16 ClNO, is oriented at a dihedral angle of 53.6 (3) towards the phenyl ring and 42.0 (9) towards the pyrrole ring of the pyrrolizine template. The phenyl ring is oriented at a dihedral angle of 45.4 (4) towards the pyrrole ring.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5600).

Comment
Based on ML3000 (Laufer et al., 2001a,b) as dual COX/LOX inhibitor, we synthesized and evaluated inhibitors for the microsomal prostaglandin E 2 synthase-1 (mPGES-1) (Liedtke et al., 2009). The title compound was synthesized to obtain a template with a reactive group in position 5 of the pyrrolizine moiety which lead to series of differend derivates of the arylpyrrolizine scaffold.
Towards the unsaturated and planar part of the pyrrolizine residue the 4-chlorophenyl residue is oriented at a dihedral angle of 42.0 (9)° and the plain phenyl ring is oriented at a dihedral angle of 45.4 (4)°. The two phenyl rings are oriented at a dihedral angle of 53.6 (3)° and both centromers show a distance of 5.07 (6) Å. The distance between the para C atoms of the rings (C13, C20) is 6.85 (0) Å.
Finally the mixture is heated to 333 K for 1 h. The mixture was cooled to 273 K, quenched by water and adjusted to pH 6 with aqueous sodium hydroxide solution 10%.
The product was collected as precipitated solid by filtration, was dissolved in dichloromethane and washed with water three times and finally dried over anhydrous sodium sulfate. The product was concentrated under vacuum and precipitated out of diisopropylic ether to yield 1.13 g (69%). Crystals of the title compound were obtained by slow evaporation of ethanol at room temperature.