تفاعل #44855

معادلة التفاعل

1-ethyl-1-methyl-4-oxopiperidinium iodide

tert-butyl 4-(aminomethyl)tetrahydro-2H-pyran-4-carboxylate

K2CO3

→

title compound

المردود 98.0%

tert-butyl 4-[(4-oxopiperidin-1-yl)methyl]tetrahydro-2H-pyran-4-carboxylate

المردود 98.0%

المذيبات

EtOH-H2O

EtOH-H2O

ظروف التفاعل

المعالجة

1. 1
   أخرىthe solvent was removed in vacuo
2. 2
   workup.ADDITIONThe residue was poured into sat. NaHCO3 aq. (200 mL)
3. 3
   استخلاصthe mixture was extracted with CH2Cl2 (200 mL×three times)
4. 4
   تجفيفThe extracts were dried over Na2SO4
5. 5
   تركيزconcentrated
6. 6
   أخرىThe residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (3:1 to 2:1)

الإجراء التجريبي

To a refluxing mixture of tert-butyl 4-(aminomethyl)tetrahydro-2H-pyran-4-carboxylate (8.00 g, 0.0372 mol, step 2) and K2CO3 (0.51 g, 0.0372 mol) in EtOH-H2O (2:1, 240 mL) was added dropwise 1-ethyl-1-methyl-4-oxopiperidinium iodide (12.0 g, 0.0445 mol, J. Org. Chem. 1995, 60, 4324-4330) in EtOH-H2O (2:1, 150 mL), and the resulting mixture was stirred at the same temperature (reflux) for 1 h. After cooling to room temperature, the solvent was removed in vacuo. The residue was poured into sat. NaHCO3 aq. (200 mL), and the mixture was extracted with CH2Cl2 (200 mL×three times). The extracts were dried over Na2SO4 and concentrated. The residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (3:1 to 2:1) to give 10.77 g (98%) of the title compound as a colorless syrup.

المصدر