Tert-butyl 4-(2-ethoxy-2-oxoethylidene)-3,3-difluoropiperidine-1-carboxylate → Tert-butyl 4-(2-ethoxy-2-oxoethyl)-3,3-difluoropiperidine-1-carboxylate

HRID 714210Notes

Reaction equation

HRID 714210 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[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][C:7]1([F:20])[F:19])[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:8][C:7]1([F:19])[F:20])[CH3:2]

Participants

4

Reactant 1

HCID 86695050Tert-butyl 4-(2-ethoxy-2-oxoethylidene)-3,3-difluoropiperidine-1-carboxylate

Product 1

HCID 73977801Tert-butyl 4-(2-ethoxy-2-oxoethyl)-3,3-difluoropiperidine-1-carboxylate

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)-3,3-difluoropiperidine-1-carboxylate (462 mg, 1.51 mmol) and Pd/C (10%, 70 mg) in dry EtOH (8 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, 1:0→1:1) and the title compound obtained as a colorless oil. LC-MS-conditions 08: tR=0.89 min; [M-CH3+H]+=293.29.

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, 1:0→1:1)

Sources & evidence

ORD record
ord-ee5104bef6234fbd91ddb226fb6f7bbd
Source dataset
uspto-grants-2015_11
Patent number
US09187435B2

Reaction notes

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