Potassium Hydroxide → 1-(1,1-Dimethylethyl) 2-[(3-carboxy-2-hydroxyphenoxy)methyl]-1-pyrrolidinecarboxylate

Participants

Reaction Conditions

Reaction Steps

tert-butyl-2-(2, 2-dimethyl-4-oxo-4,4-benzo[1,3]dioxin-8-yloxymethyl)pyrrolidine-1-carboxylate 47 (1.65 g, 4.54 mmol) was dissolved in DMSO (9.5 mL) and then 49% aqueous KOH (1.5 mL) was added to the solution to form a basic reaction mixture. This basic reaction mixture was heated at 60° C. for 40 min. After cooling to room temperature and addition of 0.5 M aqueous KHSO4 (100 mL) gave an acidic suspension. The suspension was extracted with ether (4×250 mL) and the combined extracts were washed with brine (2×50 mL) and dried (Na2SO4). Evaporation of the ether gave 1.26 g (93%) of 3-(1-tert-butoxycarbonyl pyrrolidin-2-ylmethoxy)-2-hydroxy benzoic acid 48 as a brown solid.

Provenance & Evidence