benzyl 4-[(1R,2S)-2-(2-{4-[2-(dimethylamino)-2-oxoethyl]-2,5-difluorophenoxy}ethyl)cyclopropyl]piperidine-1-carboxylate → 2-(2,5-difluoro-4-{2-[(1S,2R)-2-piperidin-4 ylcyclopropyl]ethoxy}phenyl-)-N,N-dimethylacetamide

HRID 1474717Notes

Reaction equation

HRID 1474717 reaction equation
[CH3:1][N:2]([CH3:36])[C:3](=[O:35])[CH2:4][C:5]1[C:32]([F:33])=[CH:31][C:8]([O:9][CH2:10][CH2:11][C@@H:12]2[CH2:14][C@@H:13]2[CH:15]2[CH2:20][CH2:19][N:18](C(OCC3C=CC=CC=3)=O)[CH2:17][CH2:16]2)=[C:7]([F:34])[CH:6]=1>CO.[Pd]>[F:33][C:32]1[CH:31]=[C:8]([O:9][CH2:10][CH2:11][C@@H:12]2[CH2:14][C@@H:13]2[CH:15]2[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]2)[C:7]([F:34])=[CH:6][C:5]=1[CH2:4][C:3]([N:2]([CH3:36])[CH3:1])=[O:35]

Participants

4

Reactant 1

HCID 86711198benzyl 4-[(1R,2S)-2-(2-{4-[2-(dimethylamino)-2-oxoethyl]-2,5-difluorophenoxy}ethyl)cyclopropyl]piperidine-1-carboxylate

Product 1

HCID 867112002-(2,5-difluoro-4-{2-[(1S,2R)-2-piperidin-4 ylcyclopropyl]ethoxy}phenyl-)-N,N-dimethylacetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl 4-[(1R,2S)-2-(2-{4-[2-(dimethylamino)-2-oxoethyl]-2,5-difluorophenoxy}ethyl)cyclopropyl]piperidine-1-carboxylate (226 mg, 0.451 mmol) in 2 ml anhydrous methanol at RT was added 10% palladium on carbon (25.0 mg). The reaction mixture was stirred under a hydrogen atmosphere for 2 hours. The slurry was filtered through celite, and the filtrate concentrated to afford the title compound. LC/MS (m/z): 368.4 (M+H)+.

Workup

  1. filtrationThe slurry was filtered through celite
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-39f68852289345caa99b71ca796846f6
Source dataset
uspto-grants-2015_04
Patent number
US09018224B2

Reaction notes

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