{2-[3-(Allyl-cyclopentyl-carbamoyl)-5-chloro-phenoxy]-ethyl}-pyridin-4-yl-carbamic acid tert-butyl ester → {2-[3-(Propyl-cyclopentyl-carbamoyl)-5-chloro-phenoxy]-ethyl}-pyridin-4-yl-carbamic acid tert-butyl ester

HRID 2268576Notes

Reaction equation

HRID 2268576 reaction equation
[C:1]([O:5][C:6](=[O:35])[N:7]([CH2:14][CH2:15][O:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([C:24](=[O:34])[N:25]([CH2:31][CH:32]=[CH2:33])[CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:18]=1)[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>C1(C)C=CC=CC=1.[Pd]>[C:1]([O:5][C:6](=[O:35])[N:7]([CH2:14][CH2:15][O:16][C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([C:24](=[O:34])[N:25]([CH2:31][CH2:32][CH3:33])[CH:26]2[CH2:27][CH2:28][CH2:29][CH2:30]2)[CH:18]=1)[C:8]1[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 18349220{2-[3-(Allyl-cyclopentyl-carbamoyl)-5-chloro-phenoxy]-ethyl}-pyridin-4-yl-carbamic acid tert-butyl ester

Product 1

HCID 57114405{2-[3-(Propyl-cyclopentyl-carbamoyl)-5-chloro-phenoxy]-ethyl}-pyridin-4-yl-carbamic acid tert-butyl esterYield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

A suspension of 5% Pd on carbon (0.01 g) in a solution of {2-[3-(allyl-cyclopentyl-carbamoyl)-5-chloro-phenoxy]-ethyl}-pyridin-4-yl-carbamic-acid tert-butyl ester (0.07 g) in toluene (10 ml) was stirred under an atmosphere of hydrogen for 2 h. The catalyst was filtered through diatomaceous earth and the filtrate evaporated to give the title compound as a pale yellow gum (0.07 g).

Workup

  1. filtrationThe catalyst was filtered through diatomaceous earth
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-e724841bfd764711896d325dd323c10e
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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