N-Methyl-D-glucamine → HCID 18405392, compound

Participants

Reaction Steps

The title compound was prepared according to the procedure of Example 216, with the modification that bicyclo[2.2.2]oct-1-yl-carbaldehyde (prepared by pyridinium chlorochromate oxidation of bicyclo[2.2.2]oct-1-yl-methanol (C. A. Grob, M. Ohta, E. Renk and A. Weiss, Helv. Chim. Acta 1958, 41, 1191)) was used in step d instead of cyclohexanecarboxaldehyde and 5-amino-2-methyl-benzoic acid benzyl ester replaced 3-amino-benzoic acid benzyl ester in step f. 1H NMR (300 MHz, d6-DMSO) 12.05 (1H, br s), 9.48 (1H, br s), 8.22 (1H, br s), 7.76 (1H, dd), 7.21 (1H, d), 4.76 (2H, s), 2.45 (3H, s), 2.08 (3H, br s), 1.88-1.73 (12H, m), 1.62-1.51 (13H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 60.69; H, 8.29; N, 7.28%; C38H56N4O9.2.0 H2requires: C, 60.94; H, 8.08; N, 7.48%.

Provenance & Evidence