(2E)-3-[4-Chloro-3-[[(tricyclo[3.3.1.13,7]dec-1-ylmethyl)amino]carbonyl]phenyl]-2-propenoic acid, methyl ester → HCID 12988685, compound

HRID 1816039Notes

Reaction equation

HRID 1816039 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[CH:4][C:3]=1[C:14]([NH:16][CH2:17][C:18]12[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]3)[CH2:19]1)[CH2:25]2)=[O:15]>C(OCC)(=O)C.ClCCl.[Rh]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][C:3]=1[C:14]([NH:16][CH2:17][C:18]12[CH2:19][CH:20]3[CH2:21][CH:22]([CH2:23][CH:24]([CH2:26]3)[CH2:25]1)[CH2:27]2)=[O:15]

Participants

4

Reactant 1

HCID 12988684(2E)-3-[4-Chloro-3-[[(tricyclo[3.3.1.13,7]dec-1-ylmethyl)amino]carbonyl]phenyl]-2-propenoic acid, methyl ester

Product 1

HCID 12988685HCID 12988685, compoundYield 104%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 21226138Dichloromethane ethylacetateSolvent

Procedure

5% Rhodium on carbon (0.40 g) was added to a solution of (2E)-3-[4-chloro-3-[[(tricyclo[3.3.1.13,7]dec-1-ylmethyl)amino]carbonyl]phenyl]-2-propenoic acid, methyl ester (Example 6a, 2.2 g) in ethyl acetate/dichloromethane (4:1) (160 ml) and the mixture hydrogenated at 3 bar for 24 h. The catalyst was removed by filtration and the filtrate concentrated to give the subtitled compound as an oil (2.3 g).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-06eeecd949d948499c45150f6c9f3b85
Source dataset
uspto-grants-2005_04
Patent number
US06881754B2

Reaction notes

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