Diethyl Ether → 4-((1R,2S)-2-{2-{2-fluoro-4-(methylsulfonyl)phenoxy]ethyl}cyclopropyl)piperidine

HRID 1850788Notes

Reaction equation

HRID 1850788 reaction equation
CCOCC.[F:6][C:7]1[CH:33]=[C:32]([S:34]([CH3:37])(=[O:36])=[O:35])[CH:31]=[CH:30][C:8]=1[O:9][CH2:10][CH2:11][C@@H:12]1[CH2:14][C@@H:13]1[CH:15]1[CH2:20][CH2:19][N:18](CC(C2C=CC=CC=2)=O)[CH2:17][CH2:16]1>C(O)C.[Pd]>[F:6][C:7]1[CH:33]=[C:32]([S:34]([CH3:37])(=[O:35])=[O:36])[CH:31]=[CH:30][C:8]=1[O:9][CH2:10][CH2:11][C@@H:12]1[CH2:14][C@@H:13]1[CH:15]1[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]1

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 867112062-[4-((1R,2S)-2-{2-{2-fluoro-4-(methylsulfonyl)phenoxy]ethyl}cyclopropyl)piperidine-1-yl]-1-phenylethanone

Product 1

HCID 867112054-((1R,2S)-2-{2-{2-fluoro-4-(methylsulfonyl)phenoxy]ethyl}cyclopropyl)piperidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The ether, 2-[4-((1R,2S)-2-{2-{2-fluoro-4-(methylsulfonyl)phenoxy]ethyl}cyclopropyl)piperidine-1-yl]-1-phenylethanone (740 mg, 1.62 mmol) in ethanol (25 mL) was added Palladium on carbon (10 wt. %, wet, 0.200 g), degassed (3× vacuum/H2) again and stirred under H2 at 1 atm for 64 h. The reaction mixture was filtered through a plug of celite, and the filter cake rinsed with ethanol (150 mL), ethyl acetate (150 mL), and the filtrate was concentrated under reduced pressure to provide the piperidine as a yellow oil. MS (ESI): 342 [M+H]+.

Workup

  1. customdegassed (3× vacuum/H2) again
  2. filtrationThe reaction mixture was filtered through a plug of celite
  3. washthe filter cake rinsed with ethanol (150 mL), ethyl acetate (150 mL)
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-dea09a03b409489daafa8c904e1c8e8e
Source dataset
uspto-grants-2015_02
Patent number
US08957062B2

Reaction notes

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