Water → 2-((1-(2-Adamantyloxycarbonyl)-4-phenylpiperidin-4-yl)methoxy)acetic acid

Participants

Reaction Steps

To a stirred solution of 2-adamantyl 4-((2-methoxy-2-oxoethoxy)methyl)-4-phenylpiperidine-1-carboxylate (17.5 mg, 0.04 mmol) in THF (0.5 mL) and MeOH (1 mL) were added LiOH.H2O (8.3 mg, 0.2 mmol) and water (0.5 mL). The mixture was stirred at rt for 18 h and submitted directly to prep HPLC. The product from prep HPLC (8.3 mg) was stirred gently with MP-carbonate resin (75 mg), MeOH (2 mL) and CH2Cl2 (2 mL) for 22 h. The mixture was filtered and the resin beads collected were resuspended in 20:1 CH2Cl2/TFA (5 mL) overnight. The mixture was filtered and the filtrate was concentrated to leave crude material (2.5 mg). This material was purified by prep HPLC to afford the title compound (0.75 mg). LC-MS Method 1 tR=2.12 min, m/z=428.

Provenance & Evidence