Réaction #44867

Équation de réaction

Methyl 1-(iodomethyl)cyclopentanecarboxylate

tert-butyl(piperidin-4-ylmethyl)carbamate

iPr2NEt

→

title compound

Rendement 67.2%

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

Rendement 67.2%

Solvants

N-methylpyrrolidone

NaHCO3

Conditions de réaction

Traitement

1. 1
   TempératureAfter cooling
2. 2
   Extractionextracted with AcOEt (200 mL) for three times
3. 3
   Lavagethe combined organic layer was washed with water (200 mL) and brine (200 mL)
4. 4
   SéchageThe organic layer was dried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   AutreRemoval of the solvent
8. 8
   Autregave a residue, which
9. 9
   Autrewas chromatographed on a column of silica gel eluting with EtOAc/hexane (1:1)

Mode opératoire

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.

Source