HCID 58011530, compound → HCID 58011526, compound

HRID 218393Notes

Reaction equation

HRID 218393 reaction equation
[N:1]([CH2:4][CH2:5][O:6][C@@H:7]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=1)[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)=[N+]=[N-]>CO.[OH-].[OH-].[Pd+2]>[NH2:1][CH2:4][CH2:5][O:6][C@@H:7]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[CH:22]=1)[C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:18])[CH3:19])=[O:15])[CH2:9]1

Participants

4

Reactant 1

HCID 58011530HCID 58011530, compound

Product 1

HCID 58011526HCID 58011526, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A suspension of (R)-tert-butyl 3-((R)-(2-azidoethoxy)(3-fluorophenyl)methyl)piperidine-1-carboxylate (12 g, 31.75 mmol) and Pd(OH)2/C (1.2 g) in MeOH (240 ml) was stirred under H2 for 1 hr. The mixture was filtered and evaporated under reduced pressure to give desired (R)-tert-butyl 3-((R)-(2-aminoethoxy)(3-fluorophenyl)methyl)piperidine-1-carboxylate (10 g).

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-96ec952021124cf485e5e645a3aec50f
Source dataset
uspto-grants-2012_06
Patent number
US08198453B2

Reaction notes

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