(3R,4R)-3-fluoro-4-(4-nitro-2-(trifluoromethyl)phenoxy)-1-(oxetan-3-yl)piperidine → 4-(((3R,4R)-3-fluoro-1-(oxetan-3-yl)piperidin-4-yl)oxy)-3-(trifluoromethyl)aniline

HRID 633419Notes

Reaction equation

HRID 633419 reaction equation
[F:1][C@H:2]1[C@H:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][C:10]=2[C:18]([F:21])([F:20])[F:19])[CH2:6][CH2:5][N:4]([CH:22]2[CH2:25][O:24][CH2:23]2)[CH2:3]1>CCO.[Pd]>[F:1][C@H:2]1[C@H:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=2[C:18]([F:20])([F:19])[F:21])[CH2:6][CH2:5][N:4]([CH:22]2[CH2:25][O:24][CH2:23]2)[CH2:3]1

Participants

4

Reactant 1

HCID 86704512(3R,4R)-3-fluoro-4-(4-nitro-2-(trifluoromethyl)phenoxy)-1-(oxetan-3-yl)piperidine

Product 1

HCID 867045134-(((3R,4R)-3-fluoro-1-(oxetan-3-yl)piperidin-4-yl)oxy)-3-(trifluoromethyl)anilineYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (3R,4R)-3-fluoro-4-(4-nitro-2-(trifluoromethyl)phenoxy)-1-(oxetan-3-yl)piperidine (0.9 g, 1.0 eq, 2.6 mmol) and Pd—C (10%, 0.3 g) in EtOH (50 mL) was hydrogenated at 30 psi for 1 hour. The mixture was filtered through celite and the filter cake washed with EtOH (2×10 mL). The filtrate was concentrated under vacuum to give the desired product in 90% yield. This product was taken to next step with out further purification.

Workup

  1. filtrationThe mixture was filtered through celite
  2. washthe filter cake washed with EtOH (2×10 mL)
  3. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-0c8550f2929841009aba685865fa1176
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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