Water → 1-Benzoyl-4-(4-amino-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester

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Reaction Conditions

Reaction Steps

A stirred solution of 1-benzoyl-4-(4-nitro-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester (10 g, Reference Example 9) in a mixture of ethyl acetate (324 ml) and ethanol (78 ml), at 24° C., was treated portionwise with tin chloride (30.65 g) then heated at 80° C. for 4 hours. After cooling to 24° C. the mixture was treated with water (400 ml), then with aqueous sodium bicarbonate solution (125 ml, 5%) and then filtered through a pad of celite washing twice with ethyl acetate (300 ml). The aqueous layer from the filtrate was separated and extracted twice with ethyl acetate (300 ml). The combined organic phases were dried over magnesium sulphate and evaporated (40° C. and 2.7 kPa). The residue was triturated with diethyl ether (100 ml) affording the title compound (5.48 g) as a white powder. 1H-NMR [250 MHz, (CD3)2SO at 373° K.]: δ 1.14 (t, J=7 Hz, 3H); 3.24 (m, 1H); 3.40 to 3.60 (m, 2H); 3.73 (dd, J=11 and 8.5 Hz, 1H); 3.80 to 4.00 (m, 2H); 4.08 (q, J=7 Hz, 2H); 6.58 (d, J=8 Hz, 2H); 6.98 (d, J=8 Hz, 2H); 7.40 to 7.60 (m, 5H).

Provenance & Evidence