HCID 70879987, compound → HCID 95171292, compound

HRID 714215Notes

Reaction equation

HRID 714215 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH:5]=[C:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH:7]1[F:19])[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][C@H:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])[CH2:8][C@H:7]1[F:19])[CH3:2]

Participants

4

Reactant 1

HCID 70879987HCID 70879987, compound

Product 1

HCID 95171292HCID 95171292, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar, a suspension of tert-butyl 4-(2-ethoxy-2-oxoethylidene)-3-fluoropiperidine-1-carboxylate (WO2010/056633) (2.17 g, 7.55 mmol) and Pd/C (10% Pd, 217 mg) in dry EtOH (7 mL) was stirred at rt under a H2 atmospheric pressure until completion of the reaction. The mixture was then filtered, washed with EA/EtOH, and the filtrate concentrated under reduced pressure. The crude residue was purified by FC (hept-EA, 6:1) to give cis-tert-butyl 4-(2-ethoxy-2-oxoethyl)-3-fluoropiperidine-1-carboxylate as a pale yellow oil. LC-MS-conditions 08: tR=0.86 min; [M-CH3+H]+=275.32.

Workup

  1. customIn a flame dried round-bottomed flask equipped with a magnetic stir bar
  2. customuntil completion of the reaction
  3. filtrationThe mixture was then filtered
  4. washwashed with EA/EtOH
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe crude residue was purified by FC (hept-EA, 6:1)

Sources & evidence

ORD record
ord-68dac696b55a4ed083cc4cd8ea4cf953
Source dataset
uspto-grants-2015_11
Patent number
US09187435B2

Reaction notes

Loading…