反应详情

TMPH synthesis. To a mixture of 2,2,6,6-tetramethyl-4-piperidinol (472 mg, 3.0 mmol) and methyl heptanoate (476 mg, 3.3 mmol) in 3.0 mL of dimethyl formamide was added 250 mg of powdered potassium carbonate. The resulting mixture was heated at 145˜155° C. for 64 hours under a gentle stream of N2. After cooling, the reaction mixture was partitioned between water and hexanes. The organic layer was separated, washed with water (2×) and brine, then dried over anhydrous MgSO4 and evaporated to afford the crude product as an oil. The oil was dissolved in MeOH and was then treated with 2 equivalents of conc. HCl. The solvent was removed in vacuo, and the residue was then treated with diethyl ether. The resulting solids were removed by filtration. The ethereal filtrate was concentrated in vacuo and triturated with hexane to afford 380 mg (41%) of TMPH hydrochloride. It was recrystallized from boiling ethyl acetate/hexane to afford short colorless needles, mp 113-115° C. FAB-HRMS: calculated (C16H32NO2): 270.2433 found: 270.2435.

1. temperatureAfter cooling
2. customthe reaction mixture was partitioned between water and hexanes
3. customThe organic layer was separated
4. washwashed with water (2×) and brine
5. dry with materialdried over anhydrous MgSO4
6. customevaporated
7. customto afford the crude product as an oil
8. customThe solvent was removed in vacuo
9. additionthe residue was then treated with diethyl ether
10. customThe resulting solids were removed by filtration
11. concentrationThe ethereal filtrate was concentrated in vacuo
12. customtriturated with hexane