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. Author manuscript; available in PMC: 2011 Dec 1.
Published in final edited form as: Bioorg Chem. 2010 Sep 21;38(6):247–251. doi: 10.1016/j.bioorg.2010.09.001

Scheme 2.

Scheme 2

Reagents and Conditions: (a) NaCN, H2NCH2CO2Et·HCl, DMSO/H2O 29:1 (v/v), r.t., 48 h, and then HCl(g)/Et2O (80%); (b) (i) H2/PtO2, EtOH/HCl (g), 50 psi, r.t., 6.5 h (ii) H2O·Na2CO3 (71%); (c) LiAlH4, THF, Ar, r.t., 5 h (81%); (d) (i) CH2O(aq) 37%, MeOH, r.t., 3 h, and then NaCNBH3, r.t., 4 h at pH 6-7 (maintained by adding AcOH) (ii) 1 N NaOH to pH 8-9 (94%); (e) LiAlH4, THF, Ar, reflux, 7.5 h (96%); (f) ClCO2Et, Et3N, r.t., 24 h (62%); (g) LiAlH4, THF, Ar, r.t., 24 h and then reflux 1 h (quantitative).