Reaction #44867

Reaction equation

Methyl 1-(iodomethyl)cyclopentanecarboxylate

tert-butyl(piperidin-4-ylmethyl)carbamate

iPr2NEt

→

title compound

Yield 67.2%

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

Yield 67.2%

Solvents

N-methylpyrrolidone

NaHCO3

Conditions

Workup

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

Procedure

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