Hz), 71.9 (d, J= 2.3 Hz), 111.5, 125.4, 129.6, 144.2. Anal. Calcd for C16H27N203P: C,

58.88; H, 8.34; N, 8.58. Found: C, 58.58; H, 8.33; N, 8.60.

 2-[(5S)-5-Benzyl-3-(4-methylphenyl)tetrahydro-1H-imidazol-1-yl]acetonitrile

(2.22): yellowish flakes (from EtOH); yield, 99%; mp 76-77 OC; [a]25D = +40.4 (c 1.98,

CHC13); 1H NMR 6 2.23 (s, 3H), 2.71 (dd, J= 13.0, 7.1 Hz, 1H), 2.98 (dd, J= 13.3, 5.1

Hz, 1H), 3.14 (br s, 1H), 3.36-3.41 (m, 2H), 3.63 (s, 2H), 4.05, 4.37 (AB, J= 4.0 Hz,

2H), 6.38 (d, J= 8.4 Hz, 2H), 7.02 (d, J= 8.2 Hz, 2H), 7.21-7.35 (m, 5H); 13C NMR 6

20.2, 38.6, 38.9, 52.3, 62.1, 69.9, 111.9, 114.8, 126.2, 126.7, 128.6, 128.8, 129.6, 137.5,

143.7. Anal. Calcd for C19H21N3: C, 78.31; H, 7.26; N, 14.42. Found: C, 78.45; H, 7.45;

N, 14.11.

2.4.10 Procedure for the Preparation of the Bt Intermediate 2.24 and its Substitution with
NaCN.

 A mixture of 1-ethyl-2-(4-nitrophenyl)imidazolidine (2.23, 0.66 g, 3.0 mmol), BtH

(0.36 g, 3.0 mmol), formaldehyde (37% aq solution; 0.25 g, 3.0 mmol) in CH30OHH20

(10/4 mL) was stirred at room temperature for 24 h. The precipitate formed was filtered

and recrystallized from EtOH to give 2.24.

 A mixture of 2.24 (0.35 g, 1.0 mmol) and NaCN (0.10 g, 2.0 mmol) was stirred in

DMSO (3 mL) at 25 OC for 24 hours. The mixture was diluted with CH2C12, washed with

water and dried over anhyd MgSO4. After removal of the solvent in vacuo, the residue

was purified by flash basic A1203 column chromatography with hexanes/EtOAc (6:4) as

an eluent to afford 2.25.

 1-{[3-Ethyl-2-(4-nitrophenyl)-1-imidazolidinyl]methyl}-1H-1,2,3-benzotriazole

(2.24): pale yellow microcrystals (from EtOH); yield, 85%; mp 121-122 OC; 1H NMR 6

0.92 (t, J= 7.2 Hz, 3H), 2.06-2.13 (m, 1H), 2.29-2.42 (m, 2H), 3.10-3.17 (m, 1H),