Benzyl 4-(2-(3,3-difluoroazetidin-1-yl)-2-oxoethoxy)piperidine-1-carboxylate → 1-(3,3-Difluoroazetidin-1-yl)-2-(piperidin-4-yloxy)ethanone

HRID 1091769Notes

Reaction equation

HRID 1091769 reaction equation
[F:1][C:2]1([F:26])[CH2:5][N:4]([C:6](=[O:25])[CH2:7][O:8][CH:9]2[CH2:14][CH2:13][N:12](C(OCC3C=CC=CC=3)=O)[CH2:11][CH2:10]2)[CH2:3]1>[Pd].C(O)C>[F:26][C:2]1([F:1])[CH2:5][N:4]([C:6](=[O:25])[CH2:7][O:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH2:3]1

Participants

4

Reactant 1

HCID 57791852Benzyl 4-(2-(3,3-difluoroazetidin-1-yl)-2-oxoethoxy)piperidine-1-carboxylate

Product 1

HCID 577918131-(3,3-Difluoroazetidin-1-yl)-2-(piperidin-4-yloxy)ethanoneYield 32.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Benzyl 4-(2-(3,3-difluoroazetidin-1-yl)-2-oxoethoxy)piperidine-1-carboxylate (87) (2.59 g, 7.03 mmol) and palladium on carbon (0.075 g, 0.70 mmol) were added to ethanol (40 mL). This was stirred for 3 hours under an atmosphere of H2 (1.417 g, 703.09 mmol). The reaction was filtered and the solvent evaporated to afford a viscous clear oil. The crude product was purified by distillation at 0.5 mBar, collecting fractions that distilled at 90° C. to afford the desired material as a colourless oil (0.540 g, 32.8% yield); 1H NMR (400.132 MHz, CDCl3) δ 1.49-1.40 (2H, m), 1.94-1.89 (2H, m), 2.65-2.59 (2H, m), 3.10-3.05 (2H, m), 3.44-3.38 (1H, m), 4.13 (2H, s), 4.35 (2H, t), 4.64 (2H, t); NH missing

Workup

  1. filtrationThe reaction was filtered
  2. customthe solvent evaporated
  3. customto afford a viscous clear oil
  4. distillationThe crude product was purified by distillation at 0.5 mBar
  5. customcollecting fractions
  6. distillationthat distilled at 90° C.

Sources & evidence

ORD record
ord-acb2494366f0408d915f713cf93dafa8
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

Loading…