Triphenylphosphine → 1,1-Dimethylethyl (2S)-2-[[[6-[(acetyloxy)methyl]-3-pyridinyl]oxy]methyl]-1-pyrrolidinecarboxylate

Participants

Reaction Steps

A sample of (S)-1-t-butoxycarbonyl-2-pyrrolidinemethanol (1.64 g, 8.18 mmol, prepared as in Example 15a above) and 1.05 g (6.29 mmol) of 6-acetyloxymethyl-3-hydroxypyridine, prepared as described by Deady and Dayhe, Aust. J. Chem., 2565:36 (1983), were reacted with triphenylphosphine and DEAD (8.18 mmol each) in 25 mL of THF according to the procedure of Example 14a. Workup gave 1.90 g of title compound. MS (DCI/NH3) m/e: 309 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 8.32-8.28 (m, 1H), 7.33-7.25 (m,.2H), 5.15 (s, 2H), 4.30-3.90 (m, 2H), 3.65-3.25 (m, 3H), 2.13 (s, 3H), 2.10-1.80 (m, 3H), 1.49 (s, 9H).

Provenance & Evidence