Triethylamine hydrochloride → HCID 135858785, compound

Participants

Reaction Steps

Di-tert-butyl Bicarbonate (0.091 g, 0.416 mmol) was added to a solution of (2S,3S,4R,5R)-2-(4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-5-(hydroxymethyl)pyrrolidine-3,4-diol hydrochloride (0.07 g, 0.231 mmol, synthesized according to G. B. Evans, R. N. Furneaux, G. J. Gainsford, V. L. Schramm and P. C. Tyler, Tetrahedron, 2000, 56, 3053) and triethylamine (0.065 ml, 0.462 mmol) in a mixture of water (1 ml) and MeOH (3 ml). The solution was stirred for 30 mins., then the solvent evaporated to give 116 mg of a colourless solid which consisted, as estimated by 1H NMR, of about 78 mg, 0.213 mmol of (2S,3S,4R,5R)-tert-butyl 3,4-dihydroxy-2-(4-hydroxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-5-(hydroxymethyl)pyrrolidine-1-carboxylate with the rest being triethylamine hydrochloride. This mixture was dissolved in MeOH (4 ml) and water (3 nil) and sodium periodate (0.055 g, 0.255 mmol) added. After stirring for 15 mins a precipitate formed. Sodium borohydride (0.024 g, 0.639 mmol) was added and the mixture stirred for 15 mins then filtered through Celite and the solvent evaporated. The residue was chromatographed on silica gel (CH2Cl2-MeOH, 85:15) to give (S)-tert-butyl 1,3-dihydroxypropan-2-yl(2-hydroxy-1-(4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-7-yl)ethyl)carbamate (0.072 g, 92%) as a colourless solid. 1H NMR (CD3OD) δ 7.89 (s, 1H), 7.50 (br.s 1H), 5.32 (br. s, 0.5 H), 5.08 (br. s, 0.5H), 4.28 (br.s 1H), 4.17-3.50 (br. m, 6H), 1.39 (br. d, 9H). +ESMS Found 369.1760 (M+H)+ C16H25N4O6 requires 369.1774. [α]D20 +35.8 (c, 0.505, MeOH).

Provenance & Evidence