Sodium bis(trimethylsilyl)amide → HCID 69270199, compound

Participants

Reaction Steps

Analogous to the procedure described for Example 1A, Step D, 5-[3-(tert-butyl-dimethyl-silanyloxy)-4-(3-phenoxy-phenyl)-butyl]-pyrrolidin-2-one (200 mg, 0.455 mmol) was alkylated with NaHMDS (1M in THF, 0.55 mL, 0.55 mmol) and 4-(3-bromo-propyl)-benzoic acid methyl ester (128 mg, 0.501 mmol) to yield 4-(3-{2-[3-(tert-butyl-dimethyl-silanyloxy)-4-(3-phenoxy-phenyl)-butyl]-5-oxo-pyrrolidin-1-yl}-propyl)-benzoic acid methyl ester (173.1 mg). 1H NMR (CDCl3) δ7.94 (d, 2H), 7.32 (m, 2H), 7.25–7.19 (m, 3H), 7.09 (m, 1H), 6.98 (d, 2H), 6.88–6.81 (m, 3H), 3.88 (s, 3H), 3.84 (m, 1H), 3.64 (m, 1H), 3.50 (m, 1H), 2.95 (m, 1H), 2.76–2.57 (m, 4H), 2.37 (m, 2H), 2.03 (m, 1H), 1.92–1.67 (m, 3H), 1.56 (m, 1H), 1.46–1.25 (m, 3H), 0.84 (s, 9H), −0.04 (d, 3H), −0.15 (d, 3H).

Provenance & Evidence