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To a solution of benzyl proline (41 g, 0.2 mol) in methylene chloride (200 ml) was added thionyl chloride (18.34 ml, 0.25 mol) with stirring at -20 C to -30 C over a period of 10 min. The stirring was continued at -10 C until the reaction mixture became almost transparent. Then a solution of 2-aminobenzophenone (25 g, 0.125 mol) in methylene chloride (100 ml) was added to the reaction mixture at -30 C with stirring. The stirring was continued at ambient temperature for another 10 h and a solution of sodium carbonate (40 g) in water (150 ml) was added to the reaction mixture with stirring at 0 C. The organic layer was separated, the aqueous layer extracted several times with methylene chloride and the organic solutions were combined and evaporated. The product (benzyl proline-aminobenzophenone adduct) was crystallized from ethanol and was isolated in 85% yield.
77%
To a stirred solution ofcompound 10 (4.11 g, 20 mmol) in CH2Cl2 (10 mL) was slowly added over a period of 10 min at -20 oCSOCl2 (2.85 g, 24 mmol, 1.8 mL). The stirring was continued at -10 C until the reaction mixturebecame almost transparent. At this moment, a solution of 2-aminobenzophenone (3.94 g, 20 mmol)in CH2Cl2 (10 mL) was added to the reaction mixture at -30 C and 5 min later, NEt3 (6.6 mL) was thenintroduced. The stirring was continued at room temperature for 20 hours. After adding 10% aqueousNa2CO3 (30 mL) to the reaction mixture at 0 C, the organic layer was separated and the aqueouslayer extracted with CH2Cl2 (2 × 50 mL). The organic phases were combined, dried over Na2SO4,filtered and concentrated under reduced pressure. The crude residue obtained was purified bycolumn chromatography on silica gel using cyclohexane/EtOAc 95:5 as eluent to afford 11 (5.72 g,14.9 mmol, 77%) as a yellow solid.
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