Hydrochloric Acid → HCID 46735689, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of t-butyl-4-hydroxy-1-piperidine carboxylate (1.0 g, 5.0 mmol) in anhydrous THF (5 mL) was added 4-phenoxyphenol (1.21 g, 6.5 mmol) in THF (5 mL) and triphenyl phosphine (1.57 g, 6 mmol) in THF (5 mL). The resulting mixture was cooled to 0° C. using ice-water bath and purged with nitrogen. Diisopropyl azodicarboxylate (1.21 g, 6 mmol) was dissolved in 5 mL of THF and added to above solution drop wise over period of 20 min under nitrogen. Reaction then was heated at rt for 3 h and 70° C. for 48 h. THF was removed in vacuo and crude mixture was purified by silica gel flash chromatography (10% EtOAc/Hexane) to obtain the product. To a solution of the product in dioxane (4 mL) was added 4M HCl in dioxane (10 mL) at rt and the resulting mixture was stirred for 3 h at that temperature. The solvent was removed in vacuo and residue was triturated with ether to obtain a white crystalline solid (918 mg, 68%): MS; m/z 270.5 (M+H); 1H NMR (400 MHz, DMSO-d6); δ 1.81-1.87 (m, 2H), 2.07-2.12 (m, 2H), 3.02-3.08 (m, 2H), 3.19-3.25 (m, 2H), 3.56 (s, 1H), 4.57-4.61 (m, 1H), 6.92-7.10 (m, 7H), 7.33-7.37 (m, 2H), 8.91 (s, 2H); HPLC (UV); 96%. Elemental analysis. Calc C 66.77 H 6.59 N 4.58. Found C 65.82 H 6.70 N 4.77.

Provenance & Evidence