(S)-tert-butyl 3-(5-fluoro-2-nitrophenoxy)piperidine-1-carboxylate → (S)-tert-butyl 3-(2-amino-5-fluorophenoxy)piperidine-1-carboxylate

HRID 240594Notes

Reaction equation

HRID 240594 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:22]([O-])=O)=[C:6]([CH:21]=1)[O:7][C@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]1>CO.[Pd]>[NH2:22][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:21][C:6]=1[O:7][C@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15])[CH2:9]1

Participants

4

Reactant 1

HCID 58413048(S)-tert-butyl 3-(5-fluoro-2-nitrophenoxy)piperidine-1-carboxylate

Product 1

HCID 58413089(S)-tert-butyl 3-(2-amino-5-fluorophenoxy)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-tert-butyl 3-(5-fluoro-2-nitrophenoxy)piperidine-1-carboxylate (6.41 g) in MeOH (70.0 ml) was added palladium on charcoal (600.0 mg), the mixture hydrogenated at room temperature and 50 psi. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica chromatography to give the desired product.

Workup

  1. customhydrogenated at room temperature
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica chromatography

Sources & evidence

ORD record
ord-88c079872f0242228e04ee046c9b1af7
Source dataset
uspto-grants-2014_02
Patent number
US08648068B2

Reaction notes

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