Carbon Dioxide → HCID 59383053, compound

Participants

Reaction Steps

To a solution of (R)-tert-butyl 3-((S)-1-(3-bromophenyl)-1-hydroxy-5-methoxy-pentyl)piperidine-1-carboxylate (279.1 mg, 0.61 mmol) in THF (5 mL) at −70° C. was added t-butyllithium in pentane (1.7 M, 0.71 mL, 1.22 mmol) dropwise. When the addition was complete dried carbon dioxide was bubbled through the reaction system for 10 min, and completion of reaction was confirmed by LC-MS. The solution was warmed to rt, and sat'd aq Na2CO3 solution (5 mL) was added. The organic layer was separated, and washed once with 1 N NaOH (2 mL). The combined aqueous solutions were acidified with 1 N aq HCl and extracted with EtOAc (5×5 mL). The organic layer was dried over Na2SO4, and concentrated under vacuum to give 3-((S)-1-((R)-1-(tert-butoxycarbonyl)piperidin-3-yl)-1-hydroxy-5-methoxy-pentyl)benzoic acid (152.4 mg, 59%) as a white solid. MS m/z 422 (M+H+).

Provenance & Evidence