Ammonia → 3-phenoxypiperidine

Participants

Reaction Steps

2-Chloro-N-(3-phenoxy-1-piperidinyl)adenosine was prepared according to method A as described in Example 6 by reacting 1-amino-3-phenoxypiperidine (0.60 g, 3.4 mmol) with 9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.0 g, 3.2 mmol), followed by debenzoylation of the purified product using methanolic ammonia. This provided the desired compound (0.65 g, 43%) (after column chromatography) as a foam, 1H NMR (DMSO-d6) δ 3.53-3.60 (1H, m, H-5'a), 3.64-3.72 (1H, m, H-5'b), 3.96 (1H, q, H-4'), 4.14 (1H, q, H-3'), 4.50-4.59 (1H, m, H-2' and --C--H) ), 5.07 (1H, t, 5'-0H), 5.23, 5.50 (2H, 2d, 2'- and 3'-OH), 5.84 (1H, d, H-1'), 6.79-7.32 (5H, 3m, Ar--H), 8.45 (1H, s, H-8), 9.55 (1H, s, N--H).

Provenance & Evidence