2-Methylpentane → HCID 57791809, compound

Participants

Reaction Conditions

Reaction Steps

Tert-butyl 4-hydroxypiperidine-1-carboxylate (10 g, 49.69 mmol), tetrabutylammonium hydrogensulfate (0.844 g, 2.48 mmol) and 2-chloro-1-morpholinoethanone (8.13 g, 49.69 mmol) were added to toluene (75 mL) to this was added NaOH (40 g, 400.03 mmol) in water (45 mL) and the reaction was stirred at 25° C. overnight. The reaction mixture was quenched with water (100 mL), extracted with Et2O (3×75 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford a white solid. This was redissolved in DCM and evaporated carefully to give a yellow gum, diethyl ether was added followed by iso-hexane until a cloudy solution was observed. The system was stirred to afford a solid which was collected by filtration and dried under vacuum to give the desired compound as a white solid (15.30 g, 94% yield); 1H NMR (400.132 MHz, CDCl3) δ 1.45 (9H, s), 1.58-1.49 (OH, m), 1.72-1.61 (2H, m), 1.89-1.82 (2H, m), 3.12-3.06 (2H, m), 3.61-3.54 (6H, m), 3.68-3.67 (4H, m), 3.80-3.72 (1H, m), 4.18 (2H, s).

Provenance & Evidence