反応 #44867

反応方程式

Methyl 1-(iodomethyl)cyclopentanecarboxylate

tert-butyl(piperidin-4-ylmethyl)carbamate

iPr2NEt

→

title compound

収率 67.2%

Methyl 1-[(4-{[(tert-butoxycarbonyl)amino]methyl}piperidine-1-yl)methyl]cyclopentanecarboxylate

収率 67.2%

溶媒

N-methylpyrrolidone

NaHCO3

反応条件

後処理

1. 1
   温度After cooling
2. 2
   抽出extracted with AcOEt (200 mL) for three times
3. 3
   洗浄the combined organic layer was washed with water (200 mL) and brine (200 mL)
4. 4
   乾燥The organic layer was dried over Na2SO4
5. 5
   ろ過filtered
6. 6
   濃縮concentrated
7. 7
   その他Removal of the solvent
8. 8
   その他gave a residue, which
9. 9
   その他was chromatographed on a column of silica gel eluting with EtOAc/hexane (1:1)

実験手順

A mixture of Methyl 1-(iodomethyl)cyclopentanecarboxylate(5.52 g, 0.0206 mol, Step 1), tert-butyl(piperidin-4-ylmethyl)carbamate (8.83 g, 0.0412 mol) and iPr2NEt (10.76 mL, 0.0618 mol) in N-methylpyrrolidone (70 mL) was stirred at 120° C. for 24 h. After cooling, the reaction mixture was diluted with sat. NaHCO3 aq. (200 mL), extracted with AcOEt (200 mL) for three times, and the combined organic layer was washed with water (200 mL) and brine (200 mL). The organic layer was dried over Na2SO4, filtered and concentrated. Removal of the solvent gave a residue, which was chromatographed on a column of silica gel eluting with EtOAc/hexane (1:1) to give 4.91 g (67%) of title compound as a yellow syrup.

出典