tert-butyl(3R,4R)-3-fluoro-4-(4-nitro-2-(trifluoromethyl)phenoxy)piperidine-1-carboxylate → tert-butyl(3R,4R)-4-(4-amino-2-(trifluoromethyl)phenoxy)-3-fluoropiperidine-1-carboxylate

HRID 633416Notes

Reaction equation

HRID 633416 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]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:3]1>CCO.[Pd]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C@@H:7]2[CH2:6][CH2:5][N:4]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:3][C@H:2]2[F:1])=[C:10]([C:18]([F:21])([F:19])[F:20])[CH:11]=1

Participants

4

Reactant 1

HCID 86704509tert-butyl(3R,4R)-3-fluoro-4-(4-nitro-2-(trifluoromethyl)phenoxy)piperidine-1-carboxylate

Product 1

HCID 86704510tert-butyl(3R,4R)-4-(4-amino-2-(trifluoromethyl)phenoxy)-3-fluoropiperidine-1-carboxylateYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl (3R,4R)-3-fluoro-4-(4-nitro-2-(trifluoromethyl)phenoxy)piperidine-1-carboxylate (1.2 g, 1.0 eq, 2.9 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 82% 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-c667cd9067504915ba9be594872326f5
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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