Azide → {7-[5-(1-Phenyl-cyclopentyl)-[1,2,3]triazol-1-yl]-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl}-acetic acid

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Reaction Steps

The title compound was prepared using analogous procedures described in EXAMPLE 3 from (1-ethynylcyclopentyl)benzene and enantiomerically pure propyl (7-azido-6,7,8,9-tetrahydropyrido[1,2-α]indol-10-yl)acetate, prepared by resolution of the racemic azide on a 4.6×250 mm ChiralCel OD column eluting with 15% MeOH, 15% iPrOH, 69.75% Hexanes and 0.25% Et3N at 1 mL/min and 254 nm. Retention times=10.3 and 11.5 min. EXAMPLE 6.1 and 6.2 were prepared from the chiral azide with the retention time of 10.3 and 11.5 min respectively. 1H NMR data of EXAMPLE 6.1: 1H NMR (400 MHz, DMSO-d6): δ 12.13 (s, 1 H), 7.93 (s, 1 H), 7.42 (d, 1 H), 7.36 (dd, 2 H), 7.31-7.23 (m, 3 H), 7.13 (d, 1 H), 7.07-6.97 (m, 2 H), 4.59 (s, 1 H), 3.98-3.89 (m, 1 H), 3.58-3.46 (m, 2 H), 3.03-2.92 (m, 1 H), 2.29-2.20 (m, 1 H), 2.10-2.01 (m, 1 H), 1.54-1.43 (m, 1 H). MS (+ESI) m/z: 441.2.

Provenance & Evidence