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. 2023 Aug 30;14(36):9885–9891. doi: 10.1039/d3sc03083k

Scheme 4. The preparation of saturated analogues of MGL inhibitor 7 and fendizoic acid (9) and derivatization of selected bicyclo[2.1.1]hexanes. Reagents and conditions: (a) Me2NH (2 equiv), iPrMgCl (3.5 equiv), THF, −5 °C → RT, 2 h, 95%; (b) NaH (2 equiv), MeI (2 equiv), THF, RT, 4 days, 33%; (c) PhLi (3 equiv), THF, 0 °C, 45 min, 78%; (d) LiAlH4 (2.1 equiv), Et2O, 0 °C → RT, overnight, 26%; (e) Ac2O (5 equiv), Et3N (5 equiv), DMAP (0.5 equiv), CH2Cl2, RT, overnight, 96%; (f) NaOH (3.2 equiv), EtOH : H2O (4 : 1), RT, overnight, 75%.

Scheme 4