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. Author manuscript; available in PMC: 2020 Jan 9.
Published in final edited form as: J Am Chem Soc. 2018 Dec 21;141(1):163–167. doi: 10.1021/jacs.8b13030

Figure 2.

Figure 2.

(a) Diversification of product 7i. (b) Elaboration of anti-Alzheimer drug memantine (16). Reagents and conditions: (a) Li, NH3, 60%; (b) (i) H2, Rh/Al2O3 (cat.), 83%; (ii) HCl, 48%; (c) (i) H2, Rh/Al2O3 (cat.), 83%; (ii) Li, NH3, 71%; (d) (i) H2, Rh/Al2O3 (cat.), 83%; (ii) tBuOCl, 50%; (e) (i) Boc2O; then NaOMe 79%; (ii) PhCOCH2Br, K2CO3, 81%; (iii) KOH, 64%; (f) Li, NH3, 64%; (g) H2, Rh/Al2O3 (cat.), 57%; (ii) tBuOCl, 80%; (h) (i) PhCOCH2Br, K2CO3, 71%; (ii) OsO4 (cat.), NMO, 80%; (iii) KOH, 58%.