Isoamyl Nitrite → (1S,2S,3R,5S)-3-(7-Chloro-5-(Propylthio)-3H-[1,2,3]Triazolo[4,5-d]Pyrimidin-3-Yl)-5-(2-Hydroxyethoxy)Cyclopentane-1,2-Diol

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of (1S,2S,3R,5S)-3-((5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl)amino)-5-(2-hydroxyethoxy)cyclopentane-1,2-diol (OLACINA; 0.38 g, 1 mmol) in ethyl acetate (7 mL) was added isopentyl nitrite (0.16 mL, 1.2 mmol). The reaction mixture was stirred for 1 h at 65° C. and then evaporated under reduced pressure to give a reddish powder which was recrystallized from a mixture of methyl tert-butyl ether/n-hexane to give CLTOL as a crystalline product (0.31 g, 80% yield): 99 area % by HPLC.

Provenance & Evidence