Ammonium formate → 6-(4-{3-[(1R)-3-(Diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)hexanenitrile

HRID 1433260Notes

Reaction equation

HRID 1433260 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]#[N:26])=[CH:11][C:10]=1[C@@H:27]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:28][CH2:29][N:30]([CH:34]([CH3:36])[CH3:35])[CH:31]([CH3:33])[CH3:32])C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[OH-].[Pd+2]>[CH:34]([N:30]([CH:31]([CH3:33])[CH3:32])[CH2:29][CH2:28][C@@H:27]([C:10]1[CH:11]=[C:12]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]#[N:26])[CH:13]=[CH:14][C:9]=1[OH:8])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([CH3:36])[CH3:35]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57933174HCID 57933174, compound

Product 1

HCID 579332016-(4-{3-[(1R)-3-(Diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)hexanenitrile

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

6-{[(3E)-4-{4-(Benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}but-3-en-1-yl]oxy}hexanenitrile (Preparation 24, 935 mg, 1.65 mmol) was dissolved in ethanol (20 ml) and ammonium formate (1.90 g, 30.0 mmol) and 10% palladium hydroxide on carbon (190 mg) added. The reaction was heated under reflux for 1 hour, cooled to room temperature and the reaction filtered through Arbocel™, the filtrate solvent was removed in vacuo to furnish the title compound as a colourless oil, 783 mg.

Workup

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 1 hour
  3. filtrationthe reaction filtered through Arbocel™
  4. customthe filtrate solvent was removed in vacuo

Sources & evidence

ORD record
ord-09ac21f707204456aac18f3be2a0ecda
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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