Acetic Acid → (2R,3S)-diethyl 2-((5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-3-hydroxysuccinate

Participants

Reaction Steps

A mixture of (2R,3S)-diethyl 2-amino-3-hydroxysuccinate (prepared as described in A. Breuning, R. Vicik and T. Schirmeister, Tetrahedron Asymm., 2003, 14, 3301 and Z. Tang, Z.-H. Yang, X.-H. Chen, L.-F. Cun, A.-Q. Mi, Y.-Z. Jiang and L.-Z. Gong, J. Am. Chem. Soc., 2005, 127, 9285) (0.109 g, 0.53 mmol), sodium cyanoborohydride (0.055 g, 0.88 mmol) and 5-(benzyloxymethyl)-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-carbaldehyde (0.131 g, 0.44 mmol) were evaporated from methanol (3×). The residue was dissolved in methanol (10 ml) and acetic acid added (5 drops). The reaction mixture was stirred at ambient temperature for 2 h. The reaction mixture was evaporated on to silica gel and chromatographed (ethyl acetate-petrol, 2:1 then ethyl acetate-triethylamine, 1:99) giving a colourless oil (0.166 g, 77%). 1H NMR (CDCl3) δ 8.55 (s, 1H), 7.34 (s, 1H), 7.33-7.23 (m, 5H); 5.70 (s, 2H), 4.62 (d, J=3.4 Hz, 1H), 4.48 (s, 2H), 4.23-4.15 (m, 5H), 4.10 (s, 3H), 3.99 (d, J=13.8 Hz, 1H), 3.85 (d, J=2.3 Hz, 1H), 2.25 (brs, 2H), 1.26 (t, J=7.1 Hz, 3H), 1.25 (t, J=7.1 Hz, 3H).

Provenance & Evidence