was purified by column chromatography with hexanes/EtOAc (3:1 to 1:1) as an eluent to

give 3.1a-c.

 (10aS)-2-(4-Methylphenyl)-1,2,3,5,10,10a-hexahydroimidazo[1,5-

b]isoquinoline (3.1a): colorless microcrystals (from hexanes/CHC13); yield, 76%; mp

189-190 C; []25D = -50.3 (c 1.68, CHC13); 1H NMR 6 2.26 (s, 3H), 2.91-3.06 (m, 3H),

3.24 (t, J= 8.2 Hz, 1H), 3.62-3.70 (m, 2H), 3.84 (d, J= 3.6 Hz, 1H), 4.18 (d, J= 14.4

Hz, 1H), 4.60 (d, J= 3.6 Hz, 1H), 6.45 (d, J= 8.5 Hz, 2H), 7.05-7.19 (m, 6H); 13C NMR

20.3, 33.2, 52.8, 53.0, 59.2, 71.1, 111.3, 125.3, 126.0, 126.5, 126.8, 129.1, 129.7, 133.5,

134.0, 144.3. Anal. Calcd for C18H20N2: C, 81.78; H, 7.63; N, 10.60. Found: C, 81.61; H,

7.88; N, 10.71.

 (10aS)-2-Cyclohexyl-1,2,3,5,10,10a-hexahydroimidazo[1,5-b]isoquinoline

(3.1b): colorless prism (from hexanes/CHCl3); yield, 77%; mp 101-102 OC; [a]25D

-35.5 (c 1.66, CHC13); 1H NMR 6 1.24 (br s, 5H), 1.56-1.62 (m, 1H), 1.74 (br s, 2H),

1.88 (br s, 2H), 2.31 (br s, 1H), 2.63 (t, J= 8.4 Hz, 1H), 2.76-2.93 (m, 3H), 3.17 (dd, J=

8.4, 5.5 Hz, 1H), 3.43 (d, J= 4.6 Hz, 1H), 3.56, 4.02 (AB, J= 14.3 Hz, 2H), 4.03 (d, J=

4.6 Hz, 1H), 7.04-7.26 (m, 4H); 13C NMR 6 24.7, 24.8, 26.0, 31.6, 32.2, 33.5, 52.9, 56.0,

58.8, 62.2, 74.1, 125.7, 126.2, 126.7, 129.0, 134.4, 134.8. Anal. Calcd for C17H24N2: C,

79.64; H, 9.44; N, 10.93. Found: C, 79.94; H, 9.69; N, 10.87.

 (10aS)-2-Benzyl-1,2,3,5,10,10a-hexahydroimidazo[1,5-b]isoquinoline (3.1c):

white needles (from hexanes/EtOH); yield, 85%; mp 73-74 OC; []25D = -30.3 (c 1.77,

CHC13); 1H NMR 6 2.64 (t, J= 8.7 Hz, 1H), 2.77-2.95 (m, 3H), 3.21 (dd, J= 8.7, 5.7 Hz,

1H), 3.43, 3.93 (AB, J= 5.4 Hz, 2H), 3.55, 3.99 (AB, J= 14.2 Hz, 2H), 3.84 (s, 2H),

7.04-7.16 (m, 4H), 7.23-7.39 (m, 5H); 13C NMR 6 33.5, 52.6, 59.0, 59.1, 60.6, 76.5,