4.4.5 General procedure for the Reaction of N-Acylbenzotriazoles 4.2 with Secondary
amines.

 The same procedure as used in the preparation of the secondary amides 4.4

afforded pure tertiary amides 4.5a-k.

 (4-Nitrophenyl)(tetrahydro-lH-pyrrol-l-yl)methanone (4.5d): yield, 96%; light

yellow solid; 1H NMR 6 8.17 (dd, J= 8.4, 2.0 Hz, 2H), 7.62 (dd, J= 8.4, 2.0 Hz, 2H),

3.56 (t, J= 6.3 Hz, 2H), 3.30 (t, J= 6.0 Hz, 2H), 1.99-1.74 (m, 4H); 13C NMR 6 167.0

(C=O), 148.0, 142.9, 127.9, 123.3, 49.1, 46.1, 26.1, 24.1. Anal. Calcd for CllH12N203: C,

59.99; H, 5.49; N, 12.72. Found: C, 59.85; H, 5.54; N, 12.69.

 (2-Methoxyphenyl)(tetrahydro-1H-pyrrol-l-yl)methanone (4.5f): yield, 98%;

Yellow oil; H NMR 6 7.36-7.25 (m, 2H), 7.00-6.90 (m, 2H), 3.82 (s, 3H), 3.65 (t, J=

6.3 Hz, 2H), 3.22 (t, J= 6.3 Hz, 2H), 1.97-1.83 (m, 4H); 13C NMR 6 167.7 (C=O),

155.0, 130.2, 127.5, 127.3, 120.6, 110.9, 55.4, 47.5, 45.3, 25.6, 24.4. HRMS Calcd for

C12H16N02: 206.1181 (M+1), found: 206.1178.

 1-Naphthyl(tetrahydro-1H-pyrrol-l-yl)methanone (4.5h): yield, 94%; Colorless

needles (recrystallized from benzene/hexane); 1H NMR 6 7.88-7.84 (m, 3H), 7.53-7.43

(m, 4H), 3.79 (t, J= 6.9 Hz, 2H), 3.11 (t, J= 6.9 Hz, 2H), 2.01-1.94 (m, 2H), 1.83-1.78

(m, 2H); 13C NMR 6 169.1 (C=O), 135.6, 133.4, 129.0, 128.9, 128.2, 126.8, 126.1, 125.0,

124.7, 123.5, 48.4, 45.5, 25.9, 24.5. Anal. Calcd for C15H15NO: C, 79.97; H, 6.71; N,

6.22. Found: C, 79.86; H, 6.84; N, 6.14.

 4-Pyridinyl(tetrahydro-1H-pyrrol-l-yl)methanone (4.5i): yield, 100%; Yellow

oil; 1H NMR 6 8.73-8.71 (m, 2H), 7.43-7.40 (m, 2H), 3.68 (t, J= 6.9 Hz, 2H), 3.40 (t, J