HCID 57433448, compound → HCID 86599716, compound

HRID 1726367Notes

Reaction equation

HRID 1726367 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([O:14][C:15]2[CH:20]=[C:19]([NH2:21])[CH:18]=[C:17]([F:22])[CH:16]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N1CCC[C@H](O[C:37]2[CH:42]=[C:41]([N+:43]([O-])=O)[CH:40]=[C:39](F)[CH:38]=2)C1)=O)(C)(C)C>[OH-].[OH-].[Pd+2].CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([O:14][C:15]2[CH:20]=[C:19]([NH2:21])[CH:18]=[C:17]([F:22])[CH:16]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3].[NH2:43][C:41]1[CH:42]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

5

Reactant 2

HCID 57433448HCID 57433448, compoundHCID 58732860HCID 58732860, compound

Product 1

HCID 86599716HCID 86599716, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

3-(5-Amino-3-fluoro-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester. Four cylinders charged with (S)-3-(3-fluoro-5-nitro-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester (50 g), 10% Pd(OH)2/C (5.0 g) and MeOH (300 mL) were subjected to hydrogenation under 50 psi H2. The mixture was stirred vigorously overnight. The mixture was filtered through a pad of diatomaceous earth and rinsed with methanol. The alcoholic solutions were combined and concentrated to give the aniline (S)-3-(5-amino-3-fluoro-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester as syrup in quantitative yield.

Workup

  1. filtrationThe mixture was filtered through a pad of diatomaceous earth
  2. washrinsed with methanol
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3788d99c79be43a5bae749e7eadec915
Source dataset
uspto-grants-2009_02
Patent number
US07491826B2

Reaction notes

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