Sodium bis(trimethylsilyl)amide → HCID 69270199, compound

Participants

Reaction Steps

Analogous to the procedure described for Compound 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) δ 7.94 (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