Imidazole → Tert-butyl (2S,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-hydroxypyrrolidine-1-carboxylate

Participants

Reaction Steps

To N-Boc-(2S,4R)-4-hydroxy-2-hydroxymethylpyrrolidine (0.199 g, 0.92 mmol) in DMF (2 ml) was added imidazole (0.125 g) and t-butyldimethylsilyl chloride (0.14 g). After 1.5 h, the reaction was concentrated by evaporation under reduced pressure, and the residue dissolved in diethyl ether, washed with water and brine, dried and evaporated. Purification by chromatography on silica gel eluting with 0-30% ethyl acetate in hexane gave the title material, (0.15 g, 49%). NMR (CDCl3) 0.02 (s, 3H), 0.03 (s, 3H), 0.9 (s, 9H), 1.45 (s, 9H), 1.9 (bm, 9H), 2.2 (bm, 1H), 3.3-4.0 (bm, 5H), 4.5 (m, 1H).

Provenance & Evidence