(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 719629Notes

Reaction equation

HRID 719629 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-[4chloro-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 mixture hydrogenated at 3 bar for 24 h The catalyst was removed by filtration
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-9224197d5c884dc786c54842fc3e1a02
Source dataset
uspto-grants-2006_11
Patent number
US07132457B2

Reaction notes

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