Tetrahydrofuran → HCID 96930706, compound

Participants

Reaction Steps

To a suspension of KOH (5.06 g, 90 mmol), water (60 ml) and tetrahydrofuran (200 ml) was added tert-butyl 4-(4-(benzyloxy)phenyl)-3-((4-nitrobenzoyl)oxy)piperidine-1-carboxylate (6 g, 11.3 mmol) and the reaction mixture was stirred at room temperature overnight. It was then diluted with 200 mL water and extracted twice with 200 mL ethyl acetate. The organic layer was washed with 1.5 N HCl solution and was then dried over Na2SO4, filtered, and evaporated to dryness. The crude product 4 g, (±)-rel-(3S,4R)-tert-butyl 4-(4-(benzyloxy)phenyl)-3-hydroxypiperidine-1-carboxylate), was used in the next step without further purification. LCMS (method F) RT 2.44 min (95% AP), m/z 382 (M−H) (negative mode); 1H NMR (300 MHz, DMSO-d6) δ ppm 7.29-7.44 (m, 5H), 7.71 (d, J=8.4, 2H), 6.91 (d, J=8.4, 2H), 5.06 (s, 2H), 4.45 (br s, 1H), 3.80-4.20 (m, 2H), 3.70 (br s, 1H), 2.60-3.05 (m, 3H), 1.95-2.20 (m, 1H), 1.35 (s, 9H).

Provenance & Evidence