Ammonia → HCID 44323683, compound

Participants

Reaction Steps

3-Phenylthiopiperidine was prepared from 1-(1,1-dimethylethoxycarbonyl)-3-hydroxypiperidine by the method described by Kotsuki et al., Tetrahedron Letters, 1991, 32, 4155-4158; otherwise the synthesis proceeded as described in Example 16. 1-Amino-3-phenylthiopiperidine (0.98 g, 4.0 mmol) was reacted with 9-(2',3',5'tri-O-benzoyl-β-D-ribofuranosyl)2,6-dichloro-9H-purine (2.11 g, 3.3 mmol), followed by debenzoylation of the purified product using methanolic ammonia. This provided the title 2-chloro-N-(3-phenylthio-1-piperidinyl)adenosine (0.89 g, 55%) as a foam, 1H NMR (DMSO-d6) δ 3.52-3.59 (1H, m, H-5'a), 3.63-3.71 (1H, m, H-5'b) 3.95 (1H, q, H-4'), 4.13 (1H, q, H-3'), 4.46-4.54 (1H, q, H-2'), 5.07 (1H, t, 5'-0H), 5.22, 5.49 (2H, 2d, 2'- and 3'-OH), 5.84 (1H, d, H-1'), 7.20-7.50 (5H, 2m, Ar--H), 8.43 (1H, s, H-8), 9.50 (1H, s, N--H).

Provenance & Evidence